| Saturday, February 17 |
| Former Cub Larry Cox dies in Bellefontaine, OH at the age of 43. |
| Tuesday, April 10 |
| » Defeated Phillies (0-1), 2-1 | Wrigley Field (1-0) | 1-0 | |
| » W: Les Lancaster (1-0) L: Jeff Parrett (0-1) S: Mitch Williams (1) | Second | ½ out |
| Wednesday, April 11 |
| » Major-league debuts: Willie Blair (Blue Jays) |
| Thursday, April 12 |
| » Lost to Phillies (1-1), 5-4 | Wrigley Field (1-1) | 1-1 | |
| » W: Terry Mulholland (1-0) L: Steve Wilson (0-1) S: Roger McDowell (1) | First | -- |
| » Defeated Phillies (1-2), 6-3 | Wrigley Field (2-1) | 2-1 | |
| » W: Jose Nunez (1-0) L: Pat Combs (0-1) S: Mitch Williams (2) | First | -- |
| » Major-league debuts: Dave Hollins (Phillies) |
| Friday, April 13 |
| » Defeated Pirates (2-2), 2-0 | Three Rivers Stadium (1-0) | 3-1 | Won 2 |
| » W: Greg Maddux (1-0) L: Bob Walk (0-1) S: Mitch Williams (3) | First | -- |
| Saturday, April 14 |
| » Defeated Pirates (2-3), 4-1 | Three Rivers Stadium (2-0) | 4-1 | Won 3 |
| » W: Mike Harkey (1-0) L: Doug Drabek (1-1) S: Mitch Williams (4) | First | -- |
| Sunday, April 15 |
| » Lost to Pirates (3-3), 4-3 | Three Rivers Stadium (2-1) | 4-2 | |
| » W: Bob Patterson (1-0) L: Les Lancaster (1-1) | First | -- |
| Monday, April 16 |
| » Lost to Mets (3-4), 10-1 | Wrigley Field (2-2) | 4-3 | Lost 2 |
| » W: Frank Viola (2-0) L: Steve Wilson (0-2) S: Alejandro Pena (1) | First | -- |
| Tuesday, April 17 |
| » Defeated Mets (3-5), 8-6 | Shea Stadium (1-0) | 5-3 | |
| » W: Paul Assenmacher (1-0) L: Jeff Innis (0-1) S: Dean Wilkins (1) | First | -- |
| Wednesday, April 18 |
| » Defeated Mets (3-6), 8-5 | Shea Stadium (2-0) | 6-3 | Won 2 |
| » W: Greg Maddux (2-0) L: David Cone (0-1) | First | -- |
| Thursday, April 19 |
| » Lost to Mets (4-6), 4-1 | Shea Stadium (2-1) | 6-4 | |
| » W: Dwight Gooden (1-2) L: Mike Harkey (1-1) S: John Franco (3) | First | -- |
| Friday, April 20 |
| » Lost to Pirates (6-5), 9-4 | Wrigley Field (2-3) | 6-5 | Lost 2 |
| » W: Mike Roesler (1-0) L: Mike Bielecki (0-1) | Second | 1 out |
| Saturday, April 21 |
| » Lost to Pirates (7-5), 4-3 | Wrigley Field (2-4) | 6-6 | Lost 3 |
| » W: John Smiley (1-2) L: Steve Wilson (0-3) S: Bill Landrum (1) | Second | 1 out |
| Sunday, April 22 |
| » Lost to Pirates (8-5), 3-2 | Wrigley Field (2-5) | 6-7 | Lost 4 |
| » W: Neal Heaton (3-0) L: Jose Nunez (1-1) S: Ted Power (1) | Third | 2 out |
| Tuesday, April 24 |
| » Lost to Padres (8-6), 13-3 | San Diego/Jack Murphy Stadium (0-1) | 6-8 | Lost 5 |
| » W: Dennis Rasmussen (1-0) L: Greg Maddux (2-1) | Fourth | 2½ out |
| Wednesday, April 25 |
| » Lost to Padres (9-6), 3-0 | San Diego/Jack Murphy Stadium (0-2) | 6-9 | Lost 6 |
| » W: Ed Whitson (2-0) L: Mike Bielecki (0-2) | Fifth | 3½ out |
| Thursday, April 26 |
| » Defeated Padres (9-7), 3-1 | San Diego/Jack Murphy Stadium (1-2) | 7-9 | |
| » W: Mike Harkey (2-1) L: Bruce Hurst (0-3) S: Mitch Williams (5) | Fifth | 3½ out |
| Friday, April 27 |
| » Lost to Dodgers (10-8), 5-0 | Dodger Stadium (0-1) | 7-10 | |
| » W: Fernando Valenzuela (1-2) L: Jose Nunez (1-2) | Fourth | 4½ out |
| Saturday, April 28 |
| » Lost to Dodgers (11-8), 5-4 | Dodger Stadium (0-2) | 7-11 | Lost 2 |
| » W: Ramon Martinez (2-0) L: Mitch Williams (0-1) | Fifth | 5½ out |
| Sunday, April 29 |
| » Defeated Dodgers (11-9), 4-0 | Dodger Stadium (1-2) | 8-11 | |
| » W: Greg Maddux (3-1) L: Mike Morgan (3-1) | Fifth | 5½ out |
| Monday, April 30 |
| » Major-league debuts: Jeff Shaw (Indians) |
| Tuesday, May 1 |
| » Defeated Giants (8-13), 7-4 | Candlestick Park (1-0) | 9-11 | Won 2 |
| » W: Mike Bielecki (1-2) L: Bob Knepper (0-1) S: Mitch Williams (6) | Fourth | 4½ out |
| Wednesday, May 2 |
| » Defeated Giants (8-14), 9-6 | Candlestick Park (2-0) | 10-11 | Won 3 |
| » W: Mike Harkey (3-1) L: Scott Garrelts (0-3) S: Paul Assenmacher (1) | Fourth | 3½ out |
| Saturday, May 5 |
| » Defeated Padres (10-12), 3-2 | Wrigley Field (3-5) | 11-11 | Won 4 |
| » W: Greg Maddux (4-1) L: Craig Lefferts (1-1) | Fourth | 3½ out |
| » Lost to Padres (11-12), 6-5 | Wrigley Field (3-6) | 11-12 | |
| » W: Dennis Rasmussen (2-1) L: Jose Nunez (1-3) S: Greg Harris (1) | Fourth | 3½ out |
| Sunday, May 6 |
| » Lost to Padres (12-12), 8-3 | Wrigley Field (3-7) | 11-13 | Lost 2 |
| » W: Ed Whitson (3-1) L: Mike Bielecki (1-3) | Fifth | 5 out |
| Monday, May 7 |
| » Lost to Braves (8-15), 9-8 | Wrigley Field (3-8) | 11-14 | Lost 3 |
| » W: Charlie Kerfeld (2-2) L: Mitch Williams (0-2) S: Joe Boever (3) | Fifth | 6 out |
| Tuesday, May 8 |
| » Defeated Braves (8-16), 10-8 | Wrigley Field (4-8) | 12-14 | |
| » W: Bill Long (1-1) L: Dwayne Henry (0-1) | Fifth | 6 out |
| Wednesday, May 9 |
| » Defeated Braves (8-17), 4-0 | Wrigley Field (5-8) | 13-14 | Won 2 |
| » W: Les Lancaster (2-1) L: Pete Smith (2-2) | Fifth | 6 out |
| Friday, May 11 |
| » Lost to Reds (20-6), 7-5 | Riverfront Stadium (0-1) | 13-15 | |
| » W: Norm Charlton (2-0) L: Mitch Williams (0-3) S: Rob Dibble (5) | Fifth | 6½ out |
| Saturday, May 12 |
| » Defeated Reds (20-7), 4-2 | Riverfront Stadium (1-1) | 14-15 | |
| » W: Mike Bielecki (2-3) L: Tom Browning (3-3) S: Mitch Williams (7) | Fifth | 6½ out |
| Sunday, May 13 |
| » Lost to Reds (21-7), 13-9 | Riverfront Stadium (1-2) | 14-16 | |
| » W: Rob Dibble (2-0) L: Steve Wilson (0-4) | Fifth | 7½ out |
| Monday, May 14 |
| » Lost to Braves (10-19), 3-2 | Atlanta-Fulton County Stadium (0-1) | 14-17 | Lost 2 |
| » W: Dwayne Henry (1-1) L: Mitch Williams (0-4) S: Charlie Kerfeld (2) | Fifth | 7½ out |
| Tuesday, May 15 |
| » Defeated Braves (10-20), 12-2 | Atlanta-Fulton County Stadium (1-1) | 15-17 | |
| » W: Jeff Pico (1-0) L: Pete Smith (2-3) | Fifth | 6½ out |
| Wednesday, May 16 |
| » Lost to Braves (11-20), 4-0 | Atlanta-Fulton County Stadium (1-2) | 15-18 | |
| » W: John Smoltz (2-4) L: Greg Maddux (4-2) | Fifth | 7 out |
| Thursday, May 17 |
| » Lost to Astros (13-21), 5-4 | Astrodome (0-1) | 15-19 | Lost 2 |
| » W: Dave Smith (2-2) L: Jose Nunez (1-4) | Sixth | 7 out |
| Friday, May 18 |
| » Defeated Astros (13-22), 7-0 | Astrodome (1-1) | 16-19 | |
| » W: Mike Harkey (4-1) L: Bill Gullickson (2-3) | Fifth | 7 out |
| Saturday, May 19 |
| » Defeated Astros (13-23), 4-1 | Astrodome (2-1) | 17-19 | Won 2 |
| » W: Les Lancaster (3-1) L: Jim Clancy (1-3) S: Mitch Williams (8) | Fifth | 6 out |
| Sunday, May 20 |
| » Defeated Astros (13-24), 5-1 | Astrodome (3-1) | 18-19 | Won 3 |
| » W: Shawn Boskie (1-0) L: Mike Scott (1-5) | Fourth | 5 out |
| » Major-league debuts: Shawn Boskie (Cubs) |
| Monday, May 21 |
| » Lost to Reds (26-9), 4-3 | Wrigley Field (5-9) | 18-20 | |
| » W: Jose Rijo (3-1) L: Greg Maddux (4-3) S: Randy Myers (8) | Fifth | 5 out |
| Tuesday, May 22 |
| » Defeated Reds (26-10), 2-1 | Wrigley Field (6-9) | 19-20 | |
| » W: Bill Long (2-1) L: Scott Scudder (1-1) | Fifth | 5 out |
| Wednesday, May 23 |
| » Lost to Dodgers (20-20), 4-3 | Wrigley Field (6-10) | 19-21 | |
| » W: Tim Belcher (4-3) L: Paul Assenmacher (1-1) S: Don Aase (3) | Fifth | 5 out |
| Thursday, May 24 |
| » Lost to Dodgers (21-20), 15-6 | Wrigley Field (6-11) | 19-22 | Lost 2 |
| » W: Fernando Valenzuela (4-3) L: Les Lancaster (3-2) | Fifth | 5½ out |
| Saturday, May 26 |
| » Lost to Astros (16-25), 8-1 | Wrigley Field (6-12) | 19-23 | Lost 3 |
| » W: Mike Scott (2-5) L: Shawn Boskie (1-1) | Fifth | 6½ out |
| » Lost to Astros (17-25), 12-3 | Wrigley Field (6-13) | 19-24 | Lost 4 |
| » W: Jim Deshaies (2-2) L: Greg Maddux (4-4) S: Larry Andersen (2) | Fifth | 6½ out |
| Sunday, May 27 |
| » Defeated Astros (17-26), 11-6 | Wrigley Field (7-13) | 20-24 | |
| » W: Mike Bielecki (3-3) L: Mark Portugal (1-5) | Fifth | 6½ out |
| Monday, May 28 |
| » Defeated Giants (17-28), 5-1 | Wrigley Field (8-13) | 21-24 | Won 2 |
| » W: Mike Harkey (5-1) L: Bob Knepper (3-3) S: Les Lancaster (1) | Fifth | 6½ out |
| Tuesday, May 29 |
| » Lost to Giants (18-28), 6-2 | Wrigley Field (8-14) | 21-25 | |
| » W: Don Robinson (1-0) L: Kevin Blankenship (0-1) S: Jeff Brantley (5) | Fifth | 7½ out |
| Wednesday, May 30 |
| » Lost to Giants (19-28), 4-1 | Wrigley Field (8-15) | 21-26 | Lost 2 |
| » W: John Burkett (4-1) L: Shawn Boskie (1-2) S: Steve Bedrosian (7) | Fifth | 8½ out |
| Friday, June 1 |
| » Lost to Cardinals (21-27), 6-4 | Busch Stadium II (0-1) | 21-27 | Lost 3 |
| » W: Jose DeLeon (5-3) L: Greg Maddux (4-5) S: Lee Smith (9) | Fifth | 8½ out |
| » Major-league debuts: Hector Villanueva (Cubs) |
| Saturday, June 2 |
| » Defeated Cardinals (21-28), 7-6 | Busch Stadium II (1-1) | 22-27 | |
| » W: Les Lancaster (4-2) L: Lee Smith (3-2) S: Mitch Williams (9) | Fifth | 8½ out |
| Sunday, June 3 |
| » Lost to Cardinals (22-28), 7-4 | Busch Stadium II (1-2) | 22-28 | |
| » W: Bryn Smith (6-4) L: Kevin Blankenship (0-2) | Fifth | 8½ out |
| Monday, June 4 |
| » Lost to Pirates (31-19), 6-2 | Three Rivers Stadium (2-2) | 22-29 | Lost 2 |
| » W: Bob Patterson (4-1) L: Shawn Boskie (1-3) S: Bill Landrum (8) | Sixth | 9½ out |
| Tuesday, June 5 |
| » Lost to Pirates (32-19), 6-5 | Three Rivers Stadium (2-3) | 22-30 | Lost 3 |
| » W: Stan Belinda (1-1) L: Mitch Williams (0-5) | Sixth | 10½ out |
| Wednesday, June 6 |
| » Lost to Pirates (33-19), 6-1 | Three Rivers Stadium (2-4) | 22-31 | Lost 4 |
| » W: Doug Drabek (8-2) L: Greg Maddux (4-6) | Sixth | 11½ out |
| Thursday, June 7 |
| » Lost to Phillies (28-23), 3-1 | Wrigley Field (8-16) | 22-32 | Lost 5 |
| » W: Ken Howell (7-3) L: Mike Bielecki (3-4) | Sixth | 12½ out |
| Friday, June 8 |
| » Defeated Phillies (28-24), 15-2 | Wrigley Field (9-16) | 23-32 | |
| » W: Jeff Pico (2-0) L: Terry Mulholland (3-3) | Sixth | 11½ out |
| Saturday, June 9 |
| » Defeated Phillies (28-25), 4-3 | Wrigley Field (10-16) | 24-32 | Won 2 |
| » W: Les Lancaster (5-2) L: Jeff Parrett (2-4) | Fifth | 10½ out |
| Sunday, June 10 |
| » Defeated Phillies (28-26), 7-3 | Wrigley Field (11-16) | 25-32 | Won 3 |
| » W: Steve Wilson (1-4) L: Bruce Ruffin (3-6) S: Les Lancaster (2) | Fifth | 9½ out |
| Monday, June 11 |
| » Defeated Mets (26-28), 8-5 | Wrigley Field (12-16) | 26-32 | Won 4 |
| » W: Mitch Williams (1-5) L: Alejandro Pena (1-2) S: Paul Assenmacher (2) | Fifth | 9½ out |
| Tuesday, June 12 |
| » Lost to Mets (27-28), 19-8 | Wrigley Field (12-17) | 26-33 | |
| » W: Dwight Gooden (4-5) L: Mike Bielecki (3-5) | Fifth | 10½ out |
| Wednesday, June 13 |
| » Lost to Mets (28-28), 15-10 | Wrigley Field (12-18) | 26-34 | Lost 2 |
| » W: John Franco (3-0) L: Les Lancaster (5-3) | Fifth | 12 out |
| » Lost to Mets (29-28), 9-6 | Wrigley Field (12-19) | 26-35 | Lost 3 |
| » W: Ron Darling (2-4) L: Mike Harkey (5-2) | Fifth | 12 out |
| Friday, June 15 |
| » Lost to Phillies (30-29), 6-5 | Veteran's Stadium (0-1) | 26-36 | Lost 4 |
| » W: Darrel Akerfelds (1-0) L: Jose Nunez (1-5) | Fifth | 12½ out |
| » Lost to Phillies (31-29), 7-0 | Veteran's Stadium (0-2) | 26-37 | Lost 5 |
| » W: Bruce Ruffin (4-6) L: Mike Bielecki (3-6) | Fifth | 12½ out |
| Saturday, June 16 |
| » Lost to Phillies (32-29), 2-1 | Veteran's Stadium (0-3) | 26-38 | Lost 6 |
| » W: Darrel Akerfelds (2-0) L: Greg Maddux (4-7) | Sixth | 13½ out |
| Sunday, June 17 |
| » Defeated Phillies (32-30), 5-3 | Veteran's Stadium (1-3) | 27-38 | |
| » W: Jeff Pico (3-0) L: Jeff Parrett (2-6) S: Les Lancaster (3) | Sixth | 12½ out |
| Monday, June 18 |
| » Lost to Expos (37-28), 5-1 | Stade Olympique (0-1) | 27-39 | |
| » W: Dennis Martinez (5-4) L: Mike Harkey (5-3) | Sixth | 13 out |
| Tuesday, June 19 |
| » Defeated Expos (37-29), 2-1 | Stade Olympique (1-1) | 28-39 | |
| » W: Shawn Boskie (2-3) L: Mark Gardner (3-3) S: Les Lancaster (4) | Fifth | 12 out |
| Wednesday, June 20 |
| » Lost to Expos (38-29), 3-2 | Stade Olympique (1-2) | 28-40 | |
| » W: Dale Mohorcic (1-1) L: Greg Maddux (4-8) S: Dave Schmidt (8) | Fifth | 12 out |
| Friday, June 22 |
| » Lost to Cardinals (28-39), 7-0 | Wrigley Field (12-20) | 28-41 | Lost 2 |
| » W: Joe Magrane (4-9) L: Steve Wilson (1-5) | Sixth | 12 out |
| Saturday, June 23 |
| » Lost to Cardinals (29-39), 8-7 | Wrigley Field (12-21) | 28-42 | Lost 3 |
| » W: Bob Tewksbury (2-0) L: Mike Bielecki (3-7) S: Lee Smith (11) | Sixth | 12½ out |
| Sunday, June 24 |
| » Defeated Cardinals (29-40), 3-2 | Wrigley Field (13-21) | 29-42 | |
| » W: Paul Assenmacher (2-1) L: Tom Niedenfuer (0-3) | Sixth | 12 out |
| Monday, June 25 |
| » Lost to Expos (41-30), 7-3 | Wrigley Field (13-22) | 29-43 | |
| » W: Mark Gardner (4-3) L: Shawn Boskie (2-4) S: Bill Sampen (1) | Sixth | 13 out |
| Tuesday, June 26 |
| » Lost to Expos (42-30), 6-5 | Wrigley Field (13-23) | 29-44 | Lost 2 |
| » W: Dave Schmidt (3-0) L: Les Lancaster (5-4) S: Steve Frey (4) | Sixth | 14 out |
| Wednesday, June 27 |
| » Defeated Expos (42-31), 5-3 | Wrigley Field (14-23) | 30-44 | |
| » W: Jeff Pico (4-0) L: Kevin Gross (8-5) S: Steve Wilson (1) | Fifth | 14 out |
| Thursday, June 28 |
| » Defeated Expos (42-32), 3-2 | Wrigley Field (15-23) | 31-44 | Won 2 |
| » W: Les Lancaster (6-4) L: Bill Sampen (6-1) | Fifth | 13 out |
| Friday, June 29 |
| » Defeated Padres (35-36), 3-2 | San Diego/Jack Murphy Stadium (2-2) | 32-44 | Won 3 |
| » W: Bill Long (3-1) L: Greg Harris (4-2) S: Paul Assenmacher (3) | Fifth | 12 out |
| Saturday, June 30 |
| » Defeated Padres (35-37), 7-3 | San Diego/Jack Murphy Stadium (3-2) | 33-44 | Won 4 |
| » W: Steve Wilson (2-5) L: Andy Benes (6-6) | Fifth | 12 out |
| » Major-league debuts: Rich Rodriguez (Padres) |
| Sunday, July 1 |
| » Defeated Padres (35-38), 11-10 | San Diego/Jack Murphy Stadium (4-2) | 34-44 | Won 5 |
| » W: Les Lancaster (7-4) L: Craig Lefferts (5-3) S: Bill Long (1) | Fifth | 12 out |
| Monday, July 2 |
| » Lost to Dodgers (37-39), 3-1 | Dodger Stadium (1-3) | 34-45 | |
| » W: Tim Belcher (6-6) L: Jeff Pico (4-1) | Fifth | 13 out |
| Tuesday, July 3 |
| » Lost to Dodgers (38-39), 7-6 | Dodger Stadium (1-4) | 34-46 | Lost 2 |
| » W: Mike Hartley (1-1) L: Paul Assenmacher (2-2) | Fifth | 14 out |
| » Major-league debuts: Terry Wells (Dodgers) |
| Wednesday, July 4 |
| » Defeated Dodgers (38-40), 5-3 | Dodger Stadium (2-4) | 35-46 | |
| » W: Mike Harkey (6-3) L: Fernando Valenzuela (6-7) S: Les Lancaster (5) | Fifth | 13 out |
| Friday, July 6 |
| » Defeated Giants (41-39), 5-2 | Candlestick Park (3-0) | 36-46 | Won 2 |
| » W: Shawn Boskie (3-4) L: Scott Garrelts (5-7) S: Bill Long (2) | Fifth | 13½ out |
| Saturday, July 7 |
| » Lost to Giants (42-39), 10-9 | Candlestick Park (3-1) | 36-47 | |
| » W: Jeff Brantley (3-1) L: Les Lancaster (7-5) | Fifth | 13½ out |
| Sunday, July 8 |
| » Lost to Giants (43-39), 5-3 | Candlestick Park (3-2) | 36-48 | Lost 2 |
| » W: Trevor Wilson (6-0) L: Jeff Pico (4-2) S: Jeff Brantley (13) | Fifth | 15 out |
| » Lost to Giants (44-39), 10-4 | Candlestick Park (3-3) | 36-49 | Lost 3 |
| » W: John Burkett (9-2) L: Mike Bielecki (3-8) | Fifth | 15 out |
| Thursday, July 12 |
| » Lost to Dodgers (40-43), 6-3 | Wrigley Field (15-24) | 36-50 | Lost 4 |
| » W: Fernando Valenzuela (7-7) L: Mike Harkey (6-4) S: Jay Howell (5) | Fifth | 16 out |
| Friday, July 13 |
| » Lost to Dodgers (41-43), 5-2 | Wrigley Field (15-25) | 36-51 | Lost 5 |
| » W: Ramon Martinez (10-4) L: Shawn Boskie (3-5) S: Jay Howell (6) | Fifth | 17 out |
| Saturday, July 14 |
| » Lost to Dodgers (42-43), 7-0 | Wrigley Field (15-26) | 36-52 | Lost 6 |
| » W: Mike Morgan (8-7) L: Greg Maddux (4-9) | Sixth | 18 out |
| Sunday, July 15 |
| » Defeated Dodgers (42-44), 5-1 | Wrigley Field (16-26) | 37-52 | |
| » W: Steve Wilson (3-5) L: Tim Belcher (7-7) | Fifth | 17 out |
| Monday, July 16 |
| » Defeated Padres (38-47), 4-3 | Wrigley Field (17-26) | 38-52 | Won 2 |
| » W: Mike Harkey (7-4) L: Eric Show (1-7) S: Mitch Williams (10) | Fifth | 16 out |
| Tuesday, July 17 |
| » Defeated Padres (38-48), 7-2 | Wrigley Field (18-26) | 39-52 | Won 3 |
| » W: Shawn Boskie (4-5) L: Andy Benes (6-7) | Fifth | 15 out |
| Wednesday, July 18 |
| » Defeated Padres (38-49), 4-2 | Wrigley Field (19-26) | 40-52 | Won 4 |
| » W: Greg Maddux (5-9) L: Dennis Rasmussen (7-7) S: Jeff Pico (1) | Fifth | 15 out |
| Friday, July 20 |
| » Defeated Giants (49-42), 5-4 | Wrigley Field (20-26) | 41-52 | Won 5 |
| » W: Mike Bielecki (4-8) L: Jeff Brantley (3-2) | Fifth | 15 out |
| Saturday, July 21 |
| » Defeated Giants (49-43), 3-2 | Wrigley Field (21-26) | 42-52 | Won 6 |
| » W: Mike Harkey (8-4) L: Jeff Brantley (3-3) | Fifth | 14 out |
| » Major-league debuts: Mark Leonard (Giants) |
| Sunday, July 22 |
| » Defeated Giants (49-44), 4-2 | Wrigley Field (22-26) | 43-52 | Won 7 |
| » W: Paul Assenmacher (3-2) L: Atlee Hammaker (4-5) S: Jeff Pico (2) | Fifth | 14 out |
| Monday, July 23 |
| » Defeated Cardinals (41-54), 3-1 | Busch Stadium II (2-2) | 44-52 | Won 8 |
| » W: Greg Maddux (6-9) L: Jose DeLeon (6-10) S: Mitch Williams (11) | Fifth | 13 out |
| Tuesday, July 24 |
| » Lost to Cardinals (42-54), 9-4 | Busch Stadium II (2-3) | 44-53 | |
| » W: Scott Terry (1-5) L: Steve Wilson (3-6) | Fifth | 14 out |
| Wednesday, July 25 |
| » Lost to Cardinals (43-54), 9-0 | Busch Stadium II (2-4) | 44-54 | Lost 2 |
| » W: John Tudor (9-3) L: Mike Harkey (8-5) | Fifth | 14 out |
| Thursday, July 26 |
| » Lost to Expos (54-45), 3-2 | Stade Olympique (1-3) | 44-55 | Lost 3 |
| » W: Tim Burke (1-1) L: Mitch Williams (1-6) | Fourth | 14 out |
| » Major-league debuts: Moises Alou (Expos) |
| Friday, July 27 |
| » Defeated Expos (54-46), 2-0 | Stade Olympique (2-3) | 45-55 | |
| » W: Greg Maddux (7-9) L: Bill Sampen (8-3) S: Bill Long (3) | Fifth | 14 out |
| Saturday, July 28 |
| » Defeated Expos (54-47), 10-7 | Stade Olympique (3-3) | 46-55 | Won 2 |
| » W: Bill Long (4-1) L: Tim Burke (1-2) | Fifth | 13 out |
| Sunday, July 29 |
| » Defeated Expos (54-48), 2-1 | Stade Olympique (4-3) | 47-55 | Won 3 |
| » W: Mike Harkey (9-5) L: Kevin Gross (8-8) S: Mitch Williams (12) | Fifth | 13 out |
| Tuesday, July 31 |
| » Lost to Pirates (58-41), 9-1 | Wrigley Field (22-27) | 47-56 | |
| » W: Bob Patterson (7-3) L: Shawn Boskie (4-6) | Fourth | 13 out |
| Wednesday, August 1 |
| » Defeated Pirates (58-42), 5-0 | Wrigley Field (23-27) | 48-56 | |
| » W: Greg Maddux (8-9) L: Rick Reed (2-3) | Fifth | 13 out |
| Thursday, August 2 |
| » Lost to Pirates (59-42), 8-5 | Wrigley Field (23-28) | 48-57 | |
| » W: John Smiley (5-5) L: Steve Wilson (3-7) S: Bob Walk (1) | Fifth | 14 out |
| Friday, August 3 |
| » Defeated Expos (55-51), 10-4 | Wrigley Field (24-28) | 49-57 | |
| » W: Mike Harkey (10-5) L: Mark Gardner (6-6) | Fifth | 14 out |
| Saturday, August 4 |
| » Defeated Expos (55-52), 10-2 | Wrigley Field (25-28) | 50-57 | Won 2 |
| » W: Shawn Boskie (5-6) L: Kevin Gross (8-9) | Fourth | 13 out |
| Sunday, August 5 |
| » Defeated Expos (55-53), 3-1 | Wrigley Field (26-28) | 51-57 | Won 3 |
| » W: Greg Maddux (9-9) L: Oil Can Boyd (6-4) | Fourth | 12 out |
| Tuesday, August 7 |
| » Defeated Cardinals (50-60), 5-3 | Wrigley Field (27-28) | 52-57 | Won 4 |
| » W: Paul Assenmacher (4-2) L: Scott Terry (1-6) S: Mitch Williams (13) | Fifth | 13 out |
| Wednesday, August 8 |
| » Defeated Cardinals (50-61), 4-3 | Wrigley Field (28-28) | 53-57 | Won 5 |
| » W: Bill Long (5-1) L: Tom Niedenfuer (0-5) | Fourth | 12 out |
| Thursday, August 9 |
| » Lost to Cardinals (51-61), 3-1 | Wrigley Field (28-29) | 53-58 | |
| » W: Ken Hill (3-1) L: Lance Dickson (0-1) S: Lee Smith (24) | Fifth | 12 out |
| » Major-league debuts: Lance Dickson (Cubs) |
| Friday, August 10 |
| » Lost to Mets (64-45), 5-1 | Shea Stadium (2-2) | 53-59 | Lost 2 |
| » W: Sid Fernandez (8-8) L: Greg Maddux (9-10) | Fifth | 12½ out |
| Saturday, August 11 |
| » Defeated Mets (64-46), 6-3 | Shea Stadium (3-2) | 54-59 | |
| » W: Steve Wilson (4-7) L: Ron Darling (4-7) S: Paul Assenmacher (4) | Fourth | 11½ out |
| Sunday, August 12 |
| » Defeated Mets (64-47), 10-2 | Shea Stadium (4-2) | 55-59 | Won 2 |
| » W: Mike Harkey (11-5) L: Frank Viola (15-7) | Fourth | 10½ out |
| Monday, August 13 |
| » Lost to Astros (50-65), 7-2 | Wrigley Field (28-30) | 55-60 | |
| » W: Mark Portugal (6-9) L: Lance Dickson (0-2) | Fourth | 11 out |
| Tuesday, August 14 |
| » Defeated Astros (50-66), 5-2 | Wrigley Field (29-30) | 56-60 | |
| » W: Greg Maddux (10-10) L: Mike Scott (9-11) S: Bill Long (4) | Fourth | 11 out |
| Wednesday, August 15 |
| » Lost to Astros (51-66), 8-4 | Wrigley Field (29-31) | 56-61 | |
| » W: Dave Smith (3-4) L: Jeff Pico (4-3) | Fourth | 11 out |
| Friday, August 17 |
| » Defeated Braves (44-74), 7-0 | Wrigley Field (30-31) | 57-61 | |
| » W: Mike Harkey (12-5) L: John Smoltz (9-9) | Fifth | 12 out |
| Saturday, August 18 |
| » Lost to Braves (45-74), 17-6 | Wrigley Field (30-32) | 57-62 | |
| » W: Charlie Leibrandt (5-7) L: Lance Dickson (0-3) | Fifth | 13 out |
| Sunday, August 19 |
| » Defeated Braves (45-75), 5-4 | Wrigley Field (31-32) | 58-62 | |
| » W: Greg Maddux (11-10) L: Kent Mercker (4-3) S: Paul Assenmacher (5) | Fifth | 13 out |
| Monday, August 20 |
| » Defeated Reds (68-52), 3-1 | Riverfront Stadium (2-2) | 59-62 | Won 2 |
| » W: Mike Bielecki (5-8) L: Norm Charlton (9-7) S: Bill Long (5) | Fourth | 13 out |
| Tuesday, August 21 |
| » Lost to Reds (69-52), 8-1 | Riverfront Stadium (2-3) | 59-63 | |
| » W: Rick Mahler (5-5) L: Mike Harkey (12-6) | Fourth | 13 out |
| » Major-league debuts: Dave Pavlas (Cubs) |
| Wednesday, August 22 |
| » Lost to Reds (70-52), 4-1 | Riverfront Stadium (2-4) | 59-64 | Lost 2 |
| » W: Jose Rijo (9-6) L: Jeff Pico (4-4) | Fourth | 14 out |
| Friday, August 24 |
| » Lost to Braves (48-77), 3-0 | Atlanta-Fulton County Stadium (1-3) | 59-65 | Lost 3 |
| » W: Steve Avery (3-7) L: Greg Maddux (11-11) | Fourth | 14½ out |
| Saturday, August 25 |
| » Defeated Braves (48-78), 6-3 | Atlanta-Fulton County Stadium (2-3) | 60-65 | |
| » W: Mike Bielecki (6-8) L: Tom Glavine (6-11) S: Paul Assenmacher (6) | Fourth | 13½ out |
| Sunday, August 26 |
| » Lost to Braves (49-78), 4-3 | Atlanta-Fulton County Stadium (2-4) | 60-66 | |
| » W: John Smoltz (11-9) L: Mitch Williams (1-7) | Fourth | 13½ out |
| Tuesday, August 28 |
| » Defeated Astros (57-72), 5-2 | Astrodome (4-1) | 61-66 | |
| » W: Greg Maddux (12-11) L: Bill Gullickson (8-12) | Fourth | 12½ out |
| Former Cub Larry Jackson dies in Boise, ID at the age of 60. |
| Wednesday, August 29 |
| » Lost to Astros (58-72), 1-0 | Astrodome (4-2) | 61-67 | |
| » W: Mark Portugal (8-9) L: Rick Sutcliffe (0-1) S: Larry Andersen (6) | Fourth | 13½ out |
| Thursday, August 30 |
| » Lost to Reds (75-54), 6-5 | Wrigley Field (31-33) | 61-68 | Lost 2 |
| » W: Danny Jackson (5-2) L: Mike Bielecki (6-9) S: Randy Myers (27) | Fourth | 14 out |
| Friday, August 31 |
| » Defeated Reds (75-55), 4-3 | Wrigley Field (32-33) | 62-68 | |
| » W: Bill Long (6-1) L: Randy Myers (3-4) | Fourth | 13 out |
| Saturday, September 1 |
| » Lost to Reds (76-55), 8-1 | Wrigley Field (32-34) | 62-69 | |
| » W: Rick Mahler (7-5) L: Jose Nunez (1-6) | Fourth | 13½ out |
| Sunday, September 2 |
| » Lost to Reds (77-55), 6-2 | Wrigley Field (32-35) | 62-70 | Lost 2 |
| » W: Jose Rijo (11-6) L: Greg Maddux (12-12) | Fourth | 14½ out |
| Monday, September 3 |
| » Lost to Expos (70-63), 3-2 | Stade Olympique (4-4) | 62-71 | Lost 3 |
| » W: Steve Frey (7-2) L: Randy Kramer (0-2) | Fourth | 15½ out |
| Tuesday, September 4 |
| » Defeated Expos (70-64), 3-1 | Stade Olympique (5-4) | 63-71 | |
| » W: Mike Bielecki (7-9) L: Dennis Martinez (10-10) S: Paul Assenmacher (7) | Fourth | 15 out |
| Wednesday, September 5 |
| » Lost to Phillies (63-72), 4-1 | Veteran's Stadium (1-4) | 63-72 | |
| » W: Terry Mulholland (8-8) L: Steve Wilson (4-8) S: Roger McDowell (19) | Fourth | 16½ out |
| Thursday, September 6 |
| » Defeated Phillies (63-73), 5-2 | Veteran's Stadium (2-4) | 64-72 | |
| » W: Jose Nunez (2-6) L: Jason Grimsley (1-1) S: Mitch Williams (14) | Fourth | 16½ out |
| » Major-league debuts: Chuck Malone (Phillies) Derrick May (Cubs) |
| Friday, September 7 |
| » Lost to Cardinals (63-75), 4-3 | Wrigley Field (32-36) | 64-73 | |
| » W: Bob Tewksbury (10-5) L: Greg Maddux (12-13) S: Lee Smith (29) | Fourth | 16½ out |
| Saturday, September 8 |
| » Defeated Cardinals (63-76), 5-4 | Wrigley Field (33-36) | 65-73 | |
| » W: Dave Pavlas (1-0) L: Ken Dayley (4-3) S: Paul Assenmacher (8) | Fourth | 16½ out |
| Sunday, September 9 |
| » Lost to Cardinals (64-76), 9-2 | Wrigley Field (33-37) | 65-74 | |
| » W: John Tudor (12-4) L: Mike Bielecki (7-10) | Fourth | 16½ out |
| Monday, September 10 |
| » Lost to Expos (74-66), 7-4 | Wrigley Field (33-38) | 65-75 | Lost 2 |
| » W: Chris Nabholz (5-0) L: Bill Long (6-2) S: Tim Burke (18) | Fourth | 17½ out |
| Tuesday, September 11 |
| » Defeated Expos (74-67), 11-6 | Wrigley Field (34-38) | 66-75 | |
| » W: Dave Pavlas (2-0) L: Kevin Gross (8-11) | Fourth | 17½ out |
| Wednesday, September 12 |
| » Defeated Phillies (65-77), 9-3 | Wrigley Field (35-38) | 67-75 | Won 2 |
| » W: Greg Maddux (13-13) L: Jose DeJesus (5-7) | Fourth | 16½ out |
| Thursday, September 13 |
| » Defeated Phillies (65-78), 6-5 | Wrigley Field (36-38) | 68-75 | Won 3 |
| » W: Paul Assenmacher (5-2) L: Roger McDowell (6-7) S: Les Lancaster (6) | Fourth | 15½ out |
| Friday, September 14 |
| » Lost to Cardinals (66-79), 4-2 | Busch Stadium II (2-5) | 68-76 | |
| » W: Bryn Smith (8-8) L: Mitch Williams (1-8) S: Mike Perez (1) | Fourth | 15½ out |
| Saturday, September 15 |
| » Defeated Cardinals (66-80), 6-2 | Busch Stadium II (3-5) | 69-76 | |
| » W: Les Lancaster (8-5) L: Jose DeLeon (7-17) | Fourth | 14½ out |
| Sunday, September 16 |
| » Defeated Cardinals (66-81), 8-4 | Busch Stadium II (4-5) | 70-76 | Won 2 |
| » W: Jose Nunez (3-6) L: Ken Hill (4-4) S: Mike Bielecki (1) | Fourth | 13½ out |
| Tuesday, September 18 |
| » Defeated Pirates (84-64), 8-5 | Wrigley Field (37-38) | 71-76 | Won 3 |
| » W: Greg Maddux (14-13) L: John Smiley (8-10) | Fourth | 12½ out |
| Wednesday, September 19 |
| » Lost to Pirates (85-64), 8-7 | Wrigley Field (37-39) | 71-77 | |
| » W: Doug Drabek (20-6) L: Rick Sutcliffe (0-2) S: Bob Patterson (5) | Fourth | 13½ out |
| Thursday, September 20 |
| » Lost to Pirates (86-64), 11-2 | Wrigley Field (37-40) | 71-78 | Lost 2 |
| » W: Bob Walk (6-5) L: Randy Kramer (0-3) S: Vicente Palacios (1) | Fourth | 14½ out |
| » Major-league debuts: Carlos Garcia (Pirates) |
| Friday, September 21 |
| » Defeated Mets (83-67), 4-3 | Wrigley Field (38-40) | 72-78 | |
| » W: Paul Assenmacher (6-2) L: David Cone (12-10) | Fourth | 14½ out |
| Saturday, September 22 |
| » Lost to Mets (84-67), 11-5 | Wrigley Field (38-41) | 72-79 | |
| » W: Ron Darling (6-9) L: Jose Nunez (3-7) | Fourth | 14½ out |
| Sunday, September 23 |
| » Lost to Mets (85-67), 7-3 | Wrigley Field (38-42) | 72-80 | Lost 2 |
| » W: Dwight Gooden (18-6) L: Greg Maddux (14-14) | Fourth | 15½ out |
| Monday, September 24 |
| » Defeated Mets (85-68), 4-3 | Wrigley Field (39-42) | 73-80 | |
| » W: Paul Assenmacher (7-2) L: Frank Viola (19-11) | Fourth | 15 out |
| Tuesday, September 25 |
| » Lost to Pirates (89-65), 5-3 | Three Rivers Stadium (2-5) | 73-81 | |
| » W: Doug Drabek (21-6) L: Steve Wilson (4-9) | Fourth | 16 out |
| Wednesday, September 26 |
| » Lost to Pirates (90-65), 4-3 | Three Rivers Stadium (2-6) | 73-82 | Lost 2 |
| » W: Zane Smith (12-8) L: Kevin Coffman (0-1) | Fourth | 17 out |
| Thursday, September 27 |
| » Lost to Pirates (91-65), 3-2 | Three Rivers Stadium (2-7) | 73-83 | Lost 3 |
| » W: Randy Tomlin (4-4) L: Mike Bielecki (7-11) S: Vicente Palacios (3) | Fifth | 18 out |
| Friday, September 28 |
| » Lost to Mets (89-68), 7-1 | Shea Stadium (4-3) | 73-84 | Lost 4 |
| » W: Dwight Gooden (19-6) L: Greg Maddux (14-15) | Fifth | 19 out |
| Saturday, September 29 |
| » Defeated Mets (89-69), 3-2 | Shea Stadium (5-3) | 74-84 | |
| » W: Les Lancaster (9-5) L: Frank Viola (19-12) S: Paul Assenmacher (9) | Fifth | 19 out |
| Sunday, September 30 |
| » Defeated Mets (89-70), 6-5 | Shea Stadium (6-3) | 75-84 | Won 2 |
| » W: Jose Nunez (4-7) L: John Franco (5-3) S: Mitch Williams (15) | Fifth | 19 out |
| » Major-league debuts: Chris Jelic (Mets) |
| Monday, October 1 |
| » Lost to Phillies (77-83), 7-6 | Veteran's Stadium (2-5) | 75-85 | |
| » W: Jose DeJesus (7-8) L: Kevin Coffman (0-2) S: Roger McDowell (22) | Fifth | 19 out |
| Tuesday, October 2 |
| » Defeated Phillies (77-84), 3-1 | Veteran's Stadium (3-5) | 76-85 | |
| » W: Mike Bielecki (8-11) L: Tommy Greene (3-3) S: Mitch Williams (16) | Fifth | 19 out |
| Wednesday, October 3 |
| » Defeated Phillies (77-85), 4-3 | Veteran's Stadium (4-5) | 77-85 | Won 2 |
| » W: Greg Maddux (15-15) L: Chuck McElroy (0-1) S: Paul Assenmacher (10) | Fourth | 18 out |
| Saturday, November 3 |
| Former Cub Jack Russell dies in Clearwater, FL at the age of 86. |
Game information provided by Retrosheet (www.retrosheet.org) |