| Sunday, January 27 |
| Former Cub Dale Long dies in Palm Coast, FL at the age of 65. |
| Sunday, February 24 |
| Former Cub Joe Munson dies in Drexel Hill, PA at the age of 92. |
| Monday, April 1 |
| Former Cub Frankie Gustine dies in Davenport, IA at the age of 72. |
| Thursday, April 4 |
| Former Cub Johnny Moore dies in Bradenton, FL at the age of 90. |
| Monday, April 8 |
| » Major-league debuts: Mike Timlin (Blue Jays) |
| Tuesday, April 9 |
| » Lost to Cardinals (1-0), 4-1 | Wrigley Field (0-1) | 0-1 | |
| » W: Bryn Smith (1-0) L: Danny Jackson (0-1) S: Lee Smith (1) | Fourth | 1½ out |
| » Major-league debuts: Gary Scott (Cubs) |
| Wednesday, April 10 |
| » Defeated Cardinals (1-1), 2-0 | Wrigley Field (1-1) | 1-1 | |
| » W: Greg Maddux (1-0) L: Jose DeLeon (0-1) S: Dave Smith (1) | Second | ½ out |
| Thursday, April 11 |
| » Lost to Cardinals (2-1), 5-4 | Wrigley Field (1-2) | 1-2 | |
| » W: Ken Hill (1-0) L: Mike Harkey (0-1) S: Lee Smith (2) | Third | 1½ out |
| » Major-league debuts: Heathcliff Slocumb (Cubs) |
| Former Cub Walker Cooper dies in Scottsdale, AZ at the age of 77. |
| Friday, April 12 |
| » Lost to Pirates (3-1), 3-1 | Wrigley Field (1-3) | 1-3 | Lost 2 |
| » W: John Smiley (1-0) L: Shawn Boskie (0-1) S: Vicente Palacios (1) | Fifth | 2 out |
| Saturday, April 13 |
| » Defeated Pirates (3-2), 7-3 | Wrigley Field (2-3) | 2-3 | |
| » W: Mike Bielecki (1-0) L: Doug Drabek (0-2) | Third | 1½ out |
| Sunday, April 14 |
| » Defeated Pirates (3-3), 6-4 | Wrigley Field (3-3) | 3-3 | Won 2 |
| » W: Heathcliff Slocumb (1-0) L: Stan Belinda (0-1) S: Dave Smith (2) | Second | 1½ out |
| Monday, April 15 |
| » Defeated Phillies (3-4), 5-4 | Wrigley Field (4-3) | 4-3 | Won 3 |
| » W: Greg Maddux (2-0) L: Jason Grimsley (0-1) S: Dave Smith (3) | Second | 1½ out |
| Tuesday, April 16 |
| » Defeated Phillies (3-5), 4-3 | Wrigley Field (5-3) | 5-3 | Won 4 |
| » W: Mike Bielecki (2-0) L: Mitch Williams (0-1) | Second | ½ out |
| Wednesday, April 17 |
| » Defeated Phillies (3-6), 4-1 | Wrigley Field (6-3) | 6-3 | Won 5 |
| » W: Shawn Boskie (1-1) L: Pat Combs (1-1) S: Dave Smith (4) | First | -- |
| Thursday, April 18 |
| » Defeated Pirates (5-5), 3-2 | Three Rivers Stadium (1-0) | 7-3 | Won 6 |
| » W: Rick Sutcliffe (1-0) L: Doug Drabek (0-3) S: Paul Assenmacher (1) | First | -- |
| Former Cub Sheldon Jones dies in Greenville, NC at the age of 70. |
| Friday, April 19 |
| » Lost to Pirates (6-5), 5-4 | Three Rivers Stadium (1-1) | 7-4 | |
| » W: Stan Belinda (1-1) L: Dave Smith (0-1) | First | -- |
| » Major-league debuts: Erik Pappas (Cubs) |
| Saturday, April 20 |
| » Lost to Pirates (7-5), 9-3 | Three Rivers Stadium (1-2) | 7-5 | Lost 2 |
| » W: Zane Smith (2-0) L: Greg Maddux (2-1) | First | -- |
| Sunday, April 21 |
| » Lost to Pirates (8-5), 13-12 | Three Rivers Stadium (1-3) | 7-6 | Lost 3 |
| » W: Bob Patterson (1-0) L: Mike Bielecki (2-1) | Second | 1 out |
| Monday, April 22 |
| » Lost to Cardinals (8-6), 3-2 | Busch Stadium II (0-1) | 7-7 | Lost 4 |
| » W: Juan Agosto (1-0) L: Dave Smith (0-2) | Third | 1½ out |
| Tuesday, April 23 |
| » Lost to Cardinals (9-6), 4-2 | Busch Stadium II (0-2) | 7-8 | Lost 5 |
| » W: Bob Tewksbury (2-1) L: Rick Sutcliffe (1-1) S: Lee Smith (6) | Third | 2½ out |
| Wednesday, April 24 |
| » Defeated Cardinals (9-7), 1-0 | Busch Stadium II (1-2) | 8-8 | |
| » W: Mike Bielecki (3-1) L: Jose DeLeon (1-2) S: Paul Assenmacher (2) | Third | 2½ out |
| Thursday, April 25 |
| » Lost to Reds (8-7), 6-4 | Riverfront Stadium (0-1) | 8-9 | |
| » W: Ted Power (2-1) L: Heathcliff Slocumb (1-1) S: Randy Myers (3) | Fourth | 3½ out |
| Friday, April 26 |
| » Lost to Reds (9-7), 3-1 | Riverfront Stadium (0-2) | 8-10 | Lost 2 |
| » W: Jose Rijo (1-1) L: Mike Harkey (0-2) S: Rob Dibble (3) | Third | 3½ out |
| Saturday, April 27 |
| » Defeated Reds (9-8), 8-3 | Riverfront Stadium (1-2) | 9-10 | |
| » W: Shawn Boskie (2-1) L: Norm Charlton (1-2) S: Paul Assenmacher (3) | Third | 3½ out |
| Sunday, April 28 |
| » Lost to Reds (10-8), 4-3 | Riverfront Stadium (1-3) | 9-11 | |
| » W: Chris Hammond (3-0) L: Rick Sutcliffe (1-2) S: Rob Dibble (4) | Third | 4½ out |
| Tuesday, April 30 |
| » Defeated Astros (8-11), 10-3 | Wrigley Field (7-3) | 10-11 | |
| » W: Mike Bielecki (4-1) L: Mark Portugal (2-1) | Fourth | 3½ out |
| Wednesday, May 1 |
| » Defeated Astros (8-12), 11-8 | Wrigley Field (8-3) | 11-11 | Won 2 |
| » W: Greg Maddux (3-1) L: Jim Deshaies (0-3) | Fourth | 3½ out |
| Friday, May 3 |
| » Lost to Braves (10-10), 5-2 | Atlanta-Fulton County Stadium (0-1) | 11-12 | |
| » W: Tom Glavine (3-2) L: Shawn Boskie (2-2) S: Kent Mercker (2) | Fourth | 4½ out |
| Saturday, May 4 |
| » Lost to Braves (11-10), 4-2 | Atlanta-Fulton County Stadium (0-2) | 11-13 | Lost 2 |
| » W: John Smoltz (1-3) L: Rick Sutcliffe (1-3) S: Juan Berenguer (2) | Fourth | 4½ out |
| Sunday, May 5 |
| » Defeated Braves (11-11), 9-6 | Atlanta-Fulton County Stadium (1-2) | 12-13 | |
| » W: Chuck McElroy (1-0) L: Charlie Leibrandt (2-3) S: Dave Smith (5) | Fourth | 3½ out |
| Monday, May 6 |
| » Defeated Astros (10-14), 4-3 | Astrodome (1-0) | 13-13 | Won 2 |
| » W: Greg Maddux (4-1) L: Jim Deshaies (0-4) S: Dave Smith (6) | Fourth | 3½ out |
| Tuesday, May 7 |
| » Defeated Astros (10-15), 4-3 | Astrodome (2-0) | 14-13 | Won 3 |
| » W: Bob Scanlan (1-0) L: Xavier Hernandez (0-2) S: Dave Smith (7) | Fourth | 3½ out |
| » Major-league debuts: Bob Scanlan (Cubs) |
| Wednesday, May 8 |
| » Lost to Astros (11-15), 4-2 | Astrodome (2-1) | 14-14 | |
| » W: Pete Harnisch (2-1) L: Shawn Boskie (2-3) S: Curt Schilling (5) | Fourth | 4½ out |
| Friday, May 10 |
| » Defeated Reds (13-14), 6-5 | Wrigley Field (9-3) | 15-14 | |
| » W: Rick Sutcliffe (2-3) L: Tom Browning (4-2) S: Dave Smith (8) | Fourth | 4½ out |
| Saturday, May 11 |
| » Lost to Reds (14-14), 12-2 | Wrigley Field (9-4) | 15-15 | |
| » W: Jose Rijo (2-2) L: Mike Bielecki (4-2) | Fourth | 4½ out |
| Sunday, May 12 |
| » Lost to Reds (15-14), 5-3 | Wrigley Field (9-5) | 15-16 | Lost 2 |
| » W: Jack Armstrong (3-1) L: Greg Maddux (4-2) S: Rob Dibble (8) | Fifth | 4½ out |
| Monday, May 13 |
| » Lost to Braves (16-12), 5-3 | Wrigley Field (9-6) | 15-17 | Lost 3 |
| » W: Tom Glavine (5-2) L: Shawn Boskie (2-4) | Fifth | 5 out |
| Tuesday, May 14 |
| » Defeated Braves (16-13), 5-4 | Wrigley Field (10-6) | 16-17 | |
| » W: Paul Assenmacher (1-0) L: Kent Mercker (1-2) S: Dave Smith (9) | Fourth | 5 out |
| Wednesday, May 15 |
| » Defeated Braves (16-14), 6-1 | Wrigley Field (11-6) | 17-17 | Won 2 |
| » W: Paul Assenmacher (2-0) L: Juan Berenguer (0-1) | Fourth | 5 out |
| Friday, May 17 |
| » Lost to Phillies (17-18), 1-0 | Veteran's Stadium (0-1) | 17-18 | |
| » W: Tommy Greene (2-0) L: Les Lancaster (0-1) | Fourth | 5½ out |
| Saturday, May 18 |
| » Lost to Phillies (18-18), 5-2 | Veteran's Stadium (0-2) | 17-19 | Lost 2 |
| » W: Joe Boever (3-3) L: Paul Assenmacher (2-1) S: Mitch Williams (8) | Fifth | 6 out |
| Sunday, May 19 |
| » Defeated Phillies (18-19), 2-1 | Veteran's Stadium (1-2) | 18-19 | |
| » W: Mike Bielecki (5-2) L: Roger McDowell (3-1) S: Dave Smith (10) | Fourth | 5 out |
| Tuesday, May 21 |
| » Lost to Mets (21-15), 8-6 | Shea Stadium (0-1) | 18-20 | |
| » Manager: Joe Altobelli |
| » W: Dwight Gooden (5-3) L: Rick Sutcliffe (2-4) S: John Franco (8) | Fifth | 6 out |
| Wednesday, May 22 |
| » Defeated Mets (21-16), 5-2 | Shea Stadium (1-1) | 19-20 | |
| » Manager: Jim Essian |
| » W: Greg Maddux (5-2) L: Frank Viola (5-2) | Fourth | 5 out |
| Thursday, May 23 |
| » Defeated Mets (21-17), 4-3 | Shea Stadium (2-1) | 20-20 | Won 2 |
| » W: Les Lancaster (1-1) L: John Franco (1-3) S: Paul Assenmacher (4) | Fourth | 4 out |
| Friday, May 24 |
| » Defeated Expos (19-22), 4-3 | Wrigley Field (12-6) | 21-20 | Won 3 |
| » W: Bob Scanlan (2-0) L: Mark Gardner (0-2) S: Heathcliff Slocumb (1) | Fourth | 4 out |
| Saturday, May 25 |
| » Defeated Expos (19-23), 6-1 | Wrigley Field (13-6) | 22-20 | Won 4 |
| » W: Mike Bielecki (6-2) L: Rick Mahler (1-3) S: Chuck McElroy (1) | Fourth | 4 out |
| Sunday, May 26 |
| » Defeated Expos (19-24), 8-6 | Wrigley Field (14-6) | 23-20 | Won 5 |
| » W: Les Lancaster (2-1) L: Tim Burke (3-2) S: Dave Smith (11) | Fourth | 4 out |
| Monday, May 27 |
| » Lost to Mets (23-19), 3-1 | Wrigley Field (14-7) | 23-21 | |
| » W: Frank Viola (6-2) L: Greg Maddux (5-3) S: John Franco (9) | Fourth | 5 out |
| Tuesday, May 28 |
| » Lost to Mets (24-19), 9-8 | Wrigley Field (14-8) | 23-22 | Lost 2 |
| » W: Alejandro Pena (1-0) L: Paul Assenmacher (2-2) S: John Franco (10) | Fourth | 6 out |
| » Major-league debuts: Ced Landrum (Cubs) |
| Wednesday, May 29 |
| » Lost to Mets (25-19), 8-1 | Wrigley Field (14-9) | 23-23 | Lost 3 |
| » W: David Cone (5-3) L: Bob Scanlan (2-1) | Fourth | 7 out |
| Friday, May 31 |
| » Defeated Expos (20-27), 7-2 | Stade Olympique (1-0) | 24-23 | |
| » W: Mike Bielecki (7-2) L: Dennis Martinez (6-4) S: Les Lancaster (1) | Fourth | 7 out |
| Saturday, June 1 |
| » Defeated Expos (20-28), 2-1 | Stade Olympique (2-0) | 25-23 | Won 2 |
| » W: Chuck McElroy (2-0) L: Barry Jones (2-3) S: Dave Smith (12) | Fourth | 7 out |
| Sunday, June 2 |
| » Defeated Expos (20-29), 4-3 | Stade Olympique (3-0) | 26-23 | Won 3 |
| » W: Paul Assenmacher (3-2) L: Scott Ruskin (1-1) S: Dave Smith (13) | Fourth | 7 out |
| Tuesday, June 4 |
| » Lost to Padres (27-25), 7-1 | Wrigley Field (14-10) | 26-24 | |
| » W: Andy Benes (3-6) L: Bob Scanlan (2-2) | Fourth | 7 out |
| Wednesday, June 5 |
| » Lost to Padres (28-25), 3-0 | Wrigley Field (14-11) | 26-25 | Lost 2 |
| » W: Dennis Rasmussen (2-0) L: Mike Bielecki (7-3) | Fourth | 8 out |
| Thursday, June 6 |
| » Defeated Padres (28-26), 6-2 | Wrigley Field (15-11) | 27-25 | |
| » W: Greg Maddux (6-3) L: Jose Melendez (1-1) | Fourth | 7 out |
| » Major-league debuts: Rick Wilkins (Cubs) |
| Friday, June 7 |
| » Lost to Dodgers (31-22), 3-2 | Wrigley Field (15-12) | 27-26 | |
| » W: Mike Morgan (6-4) L: Shawn Boskie (2-5) S: Jay Howell (10) | Fourth | 8 out |
| Saturday, June 8 |
| » Defeated Dodgers (31-23), 4-3 | Wrigley Field (16-12) | 28-26 | |
| » W: Chuck McElroy (3-0) L: Kevin Gross (3-5) S: Dave Smith (14) | Fourth | 7 out |
| Sunday, June 9 |
| » Lost to Dodgers (32-23), 6-3 | Wrigley Field (16-13) | 28-27 | |
| » W: Orel Hershiser (1-1) L: Danny Jackson (0-2) | Fourth | 7 out |
| Monday, June 10 |
| » Lost to Dodgers (33-23), 13-5 | Wrigley Field (16-14) | 28-28 | Lost 2 |
| » W: Ramon Martinez (10-2) L: Mike Bielecki (7-4) S: Mike Hartley (1) | Fourth | 8 out |
| Tuesday, June 11 |
| » Lost to Giants (23-35), 8-6 | Wrigley Field (16-15) | 28-29 | Lost 3 |
| » W: Kelly Downs (3-4) L: Dave Smith (0-3) S: Dave Righetti (6) | Fourth | 8½ out |
| Wednesday, June 12 |
| » Defeated Giants (23-36), 6-1 | Wrigley Field (17-15) | 29-29 | |
| » W: Shawn Boskie (3-5) L: Don Robinson (3-5) S: Dave Smith (15) | Fourth | 8½ out |
| Thursday, June 13 |
| » Defeated Giants (23-37), 4-3 | Wrigley Field (18-15) | 30-29 | Won 2 |
| » W: Mike Bielecki (8-4) L: Trevor Wilson (2-5) S: Paul Assenmacher (5) | Fourth | 7½ out |
| Friday, June 14 |
| » Defeated Padres (31-31), 7-3 | San Diego/Jack Murphy Stadium (1-0) | 31-29 | Won 3 |
| » W: Danny Jackson (1-2) L: Andy Benes (4-7) S: Dave Smith (16) | Third | 6½ out |
| Saturday, June 15 |
| » Lost to Padres (32-31), 6-2 | San Diego/Jack Murphy Stadium (1-1) | 31-30 | |
| » W: Dennis Rasmussen (3-1) L: Mike Bielecki (8-5) | Fourth | 6½ out |
| Sunday, June 16 |
| » Lost to Padres (33-31), 4-2 | San Diego/Jack Murphy Stadium (1-2) | 31-31 | Lost 2 |
| » W: Jose Melendez (2-2) L: Greg Maddux (6-4) S: Larry Andersen (2) | Fourth | 7½ out |
| Monday, June 17 |
| » Lost to Dodgers (37-25), 6-4 | Dodger Stadium (0-1) | 31-32 | Lost 3 |
| » W: Mike Morgan (7-5) L: Shawn Boskie (3-6) S: Tim Crews (4) | Fourth | 8½ out |
| Tuesday, June 18 |
| » Lost to Dodgers (38-25), 6-5 | Dodger Stadium (0-2) | 31-33 | Lost 4 |
| » W: Mike Hartley (1-0) L: Mike Bielecki (8-6) | Fourth | 9½ out |
| Wednesday, June 19 |
| » Lost to Dodgers (39-25), 9-8 | Dodger Stadium (0-3) | 31-34 | Lost 5 |
| » W: Jay Howell (2-2) L: Paul Assenmacher (3-3) | Fourth | 9½ out |
| Thursday, June 20 |
| » Lost to Giants (26-41), 4-3 | Candlestick Park (0-1) | 31-35 | Lost 6 |
| » W: Francisco Oliveras (3-2) L: Les Lancaster (2-2) S: Dave Righetti (8) | Fifth | 9½ out |
| Friday, June 21 |
| » Lost to Giants (27-41), 4-2 | Candlestick Park (0-2) | 31-36 | Lost 7 |
| » W: Kelly Downs (4-4) L: Greg Maddux (6-5) S: Dave Righetti (9) | Fifth | 10½ out |
| Saturday, June 22 |
| » Lost to Giants (28-41), 6-3 | Candlestick Park (0-3) | 31-37 | Lost 8 |
| » W: Trevor Wilson (3-6) L: Shawn Boskie (3-7) S: Francisco Oliveras (3) | Fifth | 10½ out |
| Sunday, June 23 |
| » Lost to Giants (29-41), 2-1 | Candlestick Park (0-4) | 31-38 | Lost 9 |
| » W: Jeff Brantley (1-1) L: Dave Smith (0-4) | Fifth | 10½ out |
| Tuesday, June 25 |
| » Defeated Pirates (40-27), 5-1 | Three Rivers Stadium (2-3) | 32-38 | |
| » W: Les Lancaster (3-2) L: John Smiley (8-5) | Fifth | 9½ out |
| Wednesday, June 26 |
| » Lost to Pirates (41-27), 7-6 | Three Rivers Stadium (2-4) | 32-39 | |
| » W: Bob Walk (6-0) L: Greg Maddux (6-6) S: Bill Landrum (14) | Fifth | 10½ out |
| Thursday, June 27 |
| » Lost to Pirates (42-27), 4-3 | Three Rivers Stadium (2-5) | 32-40 | Lost 2 |
| » W: Vicente Palacios (5-2) L: Paul Assenmacher (3-4) | Fifth | 11½ out |
| Friday, June 28 |
| » Lost to Cardinals (40-32), 14-6 | Wrigley Field (18-16) | 32-41 | Lost 3 |
| » W: Omar Olivares (1-1) L: Bob Scanlan (2-3) | Fifth | 12½ out |
| Saturday, June 29 |
| » Defeated Cardinals (40-33), 6-4 | Wrigley Field (19-16) | 33-41 | |
| » W: Les Lancaster (4-2) L: Bob Tewksbury (6-4) S: Paul Assenmacher (6) | Fourth | 12½ out |
| Sunday, June 30 |
| » Defeated Cardinals (40-34), 7-4 | Wrigley Field (20-16) | 34-41 | Won 2 |
| » W: Chuck McElroy (4-0) L: Jose DeLeon (3-6) | Fourth | 12½ out |
| Monday, July 1 |
| » Defeated Pirates (45-28), 6-5 | Wrigley Field (21-16) | 35-41 | Won 3 |
| » W: Bob Scanlan (3-3) L: Stan Belinda (3-2) | Fourth | 11½ out |
| Tuesday, July 2 |
| » Lost to Pirates (46-28), 13-4 | Wrigley Field (21-17) | 35-42 | |
| » W: Doug Drabek (7-8) L: Shawn Boskie (3-8) | Fourth | 12½ out |
| Former Cub Al Glossop dies in Walnut Creek, CA at the age of 77. |
| Wednesday, July 3 |
| » Lost to Pirates (47-28), 11-7 | Wrigley Field (21-18) | 35-43 | Lost 2 |
| » W: Zane Smith (9-6) L: Les Lancaster (4-3) | Fourth | 13½ out |
| » Major-league debuts: Laddie Renfroe (Cubs) |
| Thursday, July 4 |
| » Defeated Pirates (47-29), 9-8 | Wrigley Field (22-18) | 36-43 | |
| » W: Chuck McElroy (5-0) L: Bill Landrum (1-1) | Fourth | 12½ out |
| Friday, July 5 |
| » Defeated Cardinals (43-36), 5-1 | Busch Stadium II (2-2) | 37-43 | Won 2 |
| » W: Frank Castillo (1-0) L: Jose DeLeon (3-7) | Fourth | 11½ out |
| Saturday, July 6 |
| » Defeated Cardinals (43-37), 12-2 | Busch Stadium II (3-2) | 38-43 | Won 3 |
| » W: Mike Bielecki (9-6) L: Bryn Smith (7-5) | Fourth | 10½ out |
| Sunday, July 7 |
| » Lost to Cardinals (44-37), 8-7 | Busch Stadium II (3-3) | 38-44 | |
| » W: Willie Fraser (1-2) L: Laddie Renfroe (0-1) | Fourth | 11½ out |
| Thursday, July 11 |
| » Lost to Astros (35-47), 6-4 | Wrigley Field (22-19) | 38-45 | Lost 2 |
| » W: Al Osuna (5-2) L: Dave Smith (0-5) S: Mike Capel (3) | Fourth | 12½ out |
| Friday, July 12 |
| » Defeated Astros (35-48), 5-2 | Wrigley Field (23-19) | 39-45 | |
| » W: Frank Castillo (2-0) L: Mark Portugal (8-5) S: Paul Assenmacher (7) | Fourth | 12½ out |
| » Major-league debuts: Scott Servais (Astros) |
| Saturday, July 13 |
| » Defeated Astros (35-49), 4-3 | Wrigley Field (24-19) | 40-45 | Won 2 |
| » W: Les Lancaster (5-3) L: Mike Capel (1-2) | Fourth | 12½ out |
| Sunday, July 14 |
| » Defeated Astros (35-50), 4-3 | Wrigley Field (25-19) | 41-45 | Won 3 |
| » W: Mike Bielecki (10-6) L: Darryl Kile (3-3) S: Paul Assenmacher (8) | Fourth | 12½ out |
| Monday, July 15 |
| » Defeated Braves (43-41), 6-4 | Atlanta-Fulton County Stadium (2-2) | 42-45 | Won 4 |
| » W: Greg Maddux (7-6) L: Pete Smith (1-3) S: Paul Assenmacher (9) | Fourth | 12½ out |
| Tuesday, July 16 |
| » Lost to Braves (44-41), 8-5 | Atlanta-Fulton County Stadium (2-3) | 42-46 | |
| » W: Marvin Freeman (1-0) L: Bob Scanlan (3-4) S: Juan Berenguer (14) | Fourth | 13½ out |
| Wednesday, July 17 |
| » Lost to Braves (45-41), 12-2 | Atlanta-Fulton County Stadium (2-4) | 42-47 | Lost 2 |
| » W: John Smoltz (4-11) L: Les Lancaster (5-4) | Fourth | 13½ out |
| Friday, July 19 |
| » Lost to Astros (37-52), 5-2 | Astrodome (2-2) | 42-48 | Lost 3 |
| » W: Pete Harnisch (6-7) L: Bob Scanlan (3-5) S: Al Osuna (7) | Fourth | 14½ out |
| Saturday, July 20 |
| » Defeated Astros (37-53), 6-0 | Astrodome (3-2) | 43-48 | |
| » W: Greg Maddux (8-6) L: Darryl Kile (3-5) | Fourth | 13½ out |
| Sunday, July 21 |
| » Defeated Astros (37-54), 4-2 | Astrodome (4-2) | 44-48 | Won 2 |
| » W: Frank Castillo (3-0) L: Jim Clancy (0-3) | Fourth | 13½ out |
| Tuesday, July 23 |
| » Defeated Reds (45-46), 8-5 | Wrigley Field (26-19) | 45-48 | Won 3 |
| » W: Les Lancaster (6-4) L: Randy Myers (4-7) S: Paul Assenmacher (10) | Fourth | 13 out |
| Wednesday, July 24 |
| » Lost to Reds (46-46), 12-3 | Wrigley Field (26-20) | 45-49 | |
| » W: Tom Browning (11-7) L: Mike Bielecki (10-7) | Fourth | 14 out |
| Thursday, July 25 |
| » Defeated Reds (46-47), 5-4 | Wrigley Field (27-20) | 46-49 | |
| » W: Heathcliff Slocumb (2-1) L: Tim Layana (0-2) | Fourth | 13½ out |
| Friday, July 26 |
| » Lost to Braves (49-44), 6-2 | Wrigley Field (27-21) | 46-50 | |
| » W: Steve Avery (11-5) L: Frank Castillo (3-1) | Fourth | 14½ out |
| Saturday, July 27 |
| » Defeated Braves (49-45), 7-5 | Wrigley Field (28-21) | 47-50 | |
| » W: Les Lancaster (7-4) L: John Smoltz (5-12) S: Chuck McElroy (2) | Fourth | 14½ out |
| Sunday, July 28 |
| » Defeated Braves (49-46), 6-2 | Wrigley Field (29-21) | 48-50 | Won 2 |
| » W: Mike Bielecki (11-7) L: Charlie Leibrandt (9-9) S: Paul Assenmacher (11) | Fourth | 13½ out |
| Tuesday, July 30 |
| » Lost to Reds (48-49), 6-5 | Riverfront Stadium (1-4) | 48-51 | |
| » W: Rob Dibble (1-1) L: Chuck McElroy (5-1) | Fourth | 12½ out |
| Wednesday, July 31 |
| » Lost to Reds (49-49), 5-1 | Riverfront Stadium (1-5) | 48-52 | Lost 2 |
| » W: Jose Rijo (7-2) L: Frank Castillo (3-2) S: Ted Power (2) | Fourth | 12½ out |
| Friday, August 2 |
| » Defeated Mets (55-46), 4-2 | Shea Stadium (3-1) | 49-52 | |
| » W: Paul Assenmacher (4-4) L: Alejandro Pena (6-1) | Fourth | 11 out |
| Saturday, August 3 |
| » Defeated Mets (55-47), 9-2 | Shea Stadium (4-1) | 50-52 | Won 2 |
| » W: Bob Scanlan (4-5) L: Frank Viola (11-8) | Fourth | 10 out |
| Sunday, August 4 |
| » Defeated Mets (55-48), 8-3 | Shea Stadium (5-1) | 51-52 | Won 3 |
| » W: Greg Maddux (9-6) L: David Cone (10-8) | Fourth | 10 out |
| Monday, August 5 |
| » Defeated Mets (55-49), 7-2 | Shea Stadium (6-1) | 52-52 | Won 4 |
| » W: Frank Castillo (4-2) L: Pete Schourek (2-2) | Fourth | 9½ out |
| » Major-league debuts: Anthony Young (Mets) |
| Tuesday, August 6 |
| » Lost to Phillies (47-58), 6-2 | Veteran's Stadium (1-3) | 52-53 | |
| » W: Mitch Williams (4-3) L: Les Lancaster (7-5) | Fourth | 10½ out |
| Wednesday, August 7 |
| » Lost to Phillies (48-58), 5-4 | Veteran's Stadium (1-4) | 52-54 | Lost 2 |
| » W: Mitch Williams (5-3) L: Les Lancaster (7-6) | Fourth | 10½ out |
| Former Cub Jimmy Cooney dies in Warwick, RI at the age of 97. |
| Thursday, August 8 |
| » Lost to Phillies (49-58), 11-1 | Veteran's Stadium (1-5) | 52-55 | Lost 3 |
| » W: Danny Cox (4-4) L: Danny Jackson (1-3) | Fourth | 10½ out |
| Friday, August 9 |
| » Defeated Mets (57-51), 5-4 | Wrigley Field (30-21) | 53-55 | |
| » W: Greg Maddux (10-6) L: David Cone (10-9) | Fourth | 9½ out |
| Saturday, August 10 |
| » Defeated Mets (57-52), 6-2 | Wrigley Field (31-21) | 54-55 | Won 2 |
| » W: Bob Scanlan (5-5) L: Tim Burke (4-6) S: Les Lancaster (2) | Fourth | 9½ out |
| Sunday, August 11 |
| » Defeated Mets (57-53), 3-2 | Wrigley Field (32-21) | 55-55 | Won 3 |
| » W: Shawn Boskie (4-8) L: Pete Schourek (2-3) | Fourth | 9½ out |
| Monday, August 12 |
| » Defeated Mets (57-54), 3-2 | Wrigley Field (33-21) | 56-55 | Won 4 |
| » W: Les Lancaster (8-6) L: Tim Burke (4-7) | Fourth | 9½ out |
| Tuesday, August 13 |
| » Lost to Expos (45-66), 7-6 | Wrigley Field (33-22) | 56-56 | |
| » W: Bill Sampen (6-2) L: Les Lancaster (8-7) S: Jeff Fassero (5) | Fourth | 10½ out |
| Wednesday, August 14 |
| » Lost to Expos (46-66), 2-0 | Wrigley Field (33-23) | 56-57 | Lost 2 |
| » W: Brian Barnes (3-4) L: Greg Maddux (10-7) S: Barry Jones (9) | Fourth | 11½ out |
| Thursday, August 15 |
| » Defeated Expos (46-67), 7-6 | Wrigley Field (34-23) | 57-57 | |
| » W: Paul Assenmacher (5-4) L: Jeff Fassero (1-4) S: Chuck McElroy (3) | Third | 10½ out |
| Friday, August 16 |
| » Defeated Phillies (54-61), 9-1 | Wrigley Field (35-23) | 58-57 | Won 2 |
| » W: Rick Sutcliffe (3-4) L: Bruce Ruffin (3-4) | Third | 10½ out |
| Saturday, August 17 |
| » Lost to Phillies (55-61), 5-2 | Wrigley Field (35-24) | 58-58 | |
| » W: Terry Mulholland (12-10) L: Mike Bielecki (11-8) S: Mitch Williams (23) | Third | 11½ out |
| Sunday, August 18 |
| » Defeated Phillies (55-62), 7-6 | Wrigley Field (36-24) | 59-58 | |
| » W: Paul Assenmacher (6-4) L: Mitch Williams (6-4) | Third | 11½ out |
| » Major-league debuts: Braulio Castillo (Phillies) |
| Monday, August 19 |
| » Defeated Expos (47-70), 3-2 | Stade Olympique (4-0) | 60-58 | Won 2 |
| » W: Paul Assenmacher (7-4) L: Bill Sampen (6-3) | Third | 11 out |
| Tuesday, August 20 |
| » Lost to Expos (48-70), 4-2 | Stade Olympique (4-1) | 60-59 | |
| » W: Chris Haney (2-4) L: Bob Scanlan (5-6) S: Mel Rojas (1) | Third | 11 out |
| Wednesday, August 21 |
| » Defeated Expos (48-71), 3-1 | Stade Olympique (5-1) | 61-59 | |
| » W: Rick Sutcliffe (4-4) L: Chris Nabholz (2-6) S: Les Lancaster (3) | Third | 10 out |
| Friday, August 23 |
| » Defeated Padres (58-64), 5-4 | Wrigley Field (37-24) | 62-59 | Won 2 |
| » W: Les Lancaster (9-7) L: Craig Lefferts (0-5) | Third | 9½ out |
| Saturday, August 24 |
| » Lost to Padres (59-64), 4-1 | Wrigley Field (37-25) | 62-60 | |
| » W: Andy Benes (9-10) L: Greg Maddux (10-8) S: Jose Melendez (1) | Third | 9½ out |
| Sunday, August 25 |
| » Lost to Padres (60-64), 12-9 | Wrigley Field (37-26) | 62-61 | Lost 2 |
| » W: Mike Maddux (5-2) L: Bob Scanlan (5-7) S: Jose Melendez (2) | Third | 10½ out |
| Monday, August 26 |
| » Lost to Dodgers (69-55), 4-3 | Wrigley Field (37-27) | 62-62 | Lost 3 |
| » W: Jim Gott (3-3) L: Chuck McElroy (5-2) S: Jay Howell (14) | Third | 10½ out |
| Tuesday, August 27 |
| » Defeated Dodgers (69-56), 2-1 | Wrigley Field (38-27) | 63-62 | |
| » W: Frank Castillo (5-2) L: Ramon Martinez (15-9) | Third | 10½ out |
| Wednesday, August 28 |
| » Defeated Giants (60-66), 8-6 | Candlestick Park (1-4) | 64-62 | Won 2 |
| » W: Mike Bielecki (12-8) L: Paul McClellan (3-2) S: Paul Assenmacher (12) | Third | 10½ out |
| Thursday, August 29 |
| » Defeated Giants (60-67), 5-4 | Candlestick Park (2-4) | 65-62 | Won 3 |
| » W: Greg Maddux (11-8) L: Francisco Oliveras (4-4) | Third | 10½ out |
| Friday, August 30 |
| » Lost to Dodgers (70-58), 2-0 | Dodger Stadium (0-4) | 65-63 | |
| » W: Tim Belcher (9-8) L: Danny Jackson (1-4) | Third | 11½ out |
| Saturday, August 31 |
| » Lost to Dodgers (71-58), 3-2 | Dodger Stadium (0-5) | 65-64 | Lost 2 |
| » W: Roger McDowell (5-8) L: Paul Assenmacher (7-5) S: Jay Howell (15) | Third | 12½ out |
| Sunday, September 1 |
| » Lost to Dodgers (72-58), 12-3 | Dodger Stadium (0-6) | 65-65 | Lost 3 |
| » W: Ramon Martinez (16-9) L: Frank Castillo (5-3) | Third | 12½ out |
| » Major-league debuts: Tom Goodwin and Eric Karros (Dodgers) |
| Monday, September 2 |
| » Defeated Padres (64-68), 10-8 | San Diego/Jack Murphy Stadium (2-2) | 66-65 | |
| » W: Chuck McElroy (6-2) L: Jose Melendez (6-5) | Third | 12½ out |
| » Major-league debuts: Jeremy Hernandez (Padres) |
| Tuesday, September 3 |
| » Lost to Padres (65-68), 4-1 | San Diego/Jack Murphy Stadium (2-3) | 66-66 | |
| » W: Andy Benes (11-10) L: Greg Maddux (11-9) | Third | 13½ out |
| Wednesday, September 4 |
| » Lost to Padres (66-68), 5-1 | San Diego/Jack Murphy Stadium (2-4) | 66-67 | Lost 2 |
| » W: Dennis Rasmussen (5-11) L: Danny Jackson (1-5) | Third | 14½ out |
| Friday, September 6 |
| » Defeated Giants (62-72), 3-2 | Wrigley Field (39-27) | 67-67 | |
| » W: Frank Castillo (6-3) L: Bryan Hickerson (1-1) S: Dave Smith (17) | Third | 14 out |
| Saturday, September 7 |
| » Defeated Giants (62-73), 2-1 | Wrigley Field (40-27) | 68-67 | Won 2 |
| » W: Mike Bielecki (13-8) L: Paul McClellan (3-3) S: Paul Assenmacher (13) | Third | 13 out |
| Sunday, September 8 |
| » Lost to Giants (63-73), 4-3 | Wrigley Field (40-28) | 68-68 | |
| » W: Trevor Wilson (10-9) L: Greg Maddux (11-10) S: Dave Righetti (21) | Third | 13 out |
| » Major-league debuts: Rey Sanchez (Cubs) |
| Monday, September 9 |
| » Lost to Pirates (82-55), 12-10 | Wrigley Field (40-29) | 68-69 | Lost 2 |
| » W: Stan Belinda (5-5) L: Dave Smith (0-6) S: Rosario Rodriguez (3) | Third | 14 out |
| Tuesday, September 10 |
| » Defeated Pirates (82-56), 6-2 | Wrigley Field (41-29) | 69-69 | |
| » W: Rick Sutcliffe (5-4) L: Randy Tomlin (8-5) S: Bob Scanlan (1) | Third | 13 out |
| Wednesday, September 11 |
| » Lost to Mets (67-72), 4-1 | Wrigley Field (41-30) | 69-70 | |
| » W: Tony Castillo (2-1) L: Frank Castillo (6-4) S: John Franco (25) | Third | 14 out |
| Thursday, September 12 |
| » Lost to Mets (68-72), 6-3 | Wrigley Field (41-31) | 69-71 | Lost 2 |
| » W: Anthony Young (2-1) L: Mike Bielecki (13-9) S: Wally Whitehurst (1) | Third | 14 out |
| Friday, September 13 |
| » Lost to Expos (62-78), 3-2 | Wrigley Field (41-32) | 69-72 | Lost 3 |
| » W: Dennis Martinez (14-9) L: Bob Scanlan (5-8) S: Barry Jones (13) | Third | 15 out |
| Saturday, September 14 |
| » Defeated Expos (62-79), 7-5 | Wrigley Field (42-32) | 70-72 | |
| » W: Bob Scanlan (6-8) L: Barry Jones (3-9) | Third | 15 out |
| Sunday, September 15 |
| » Lost to Expos (63-79), 6-5 |