| Wednesday, January 15 |
| Former Cub Charlie Gassaway dies in Miami, FL at the age of 74. |
| Thursday, January 30 |
| Former Cub Coaker Triplett dies in Boone, NC at the age of 81. |
| Tuesday, April 7 |
| » Defeated Phillies (0-1), 4-3 | Veteran's Stadium (1-0) | 1-0 | |
| » W: Greg Maddux (1-0) L: Terry Mulholland (0-1) S: Chuck McElroy (1) | First | -- |
| Wednesday, April 8 |
| » Lost to Phillies (1-1), 11-3 | Veteran's Stadium (1-1) | 1-1 | |
| » W: Tommy Greene (1-0) L: Danny Jackson (0-1) | Third | 1 out |
| » Major-league debuts: Julio Peguero (Phillies) |
| Thursday, April 9 |
| » Lost to Phillies (2-1), 7-1 | Veteran's Stadium (1-2) | 1-2 | Lost 2 |
| » W: Danny Cox (1-0) L: Mike Morgan (0-1) | Third | 1 out |
| » Major-league debuts: Ben Rivera (Phillies) |
| Friday, April 10 |
| » Lost to Cardinals (3-2), 2-1 | Wrigley Field (0-1) | 1-3 | Lost 3 |
| » W: Cris Carpenter (1-0) L: Paul Assenmacher (0-1) S: Lee Smith (1) | Fifth | 2 out |
| Saturday, April 11 |
| » Defeated Cardinals (3-3), 5-1 | Wrigley Field (1-1) | 2-3 | |
| » W: Shawn Boskie (1-0) L: Jose DeLeon (0-1) S: Chuck McElroy (2) | Third | 1 out |
| Sunday, April 12 |
| » Defeated Cardinals (3-4), 4-2 | Wrigley Field (2-1) | 3-3 | Won 2 |
| » W: Greg Maddux (2-0) L: Omar Olivares (1-1) S: Heathcliff Slocumb (1) | Second | 1 out |
| Tuesday, April 14 |
| » Lost to Pirates (5-2), 3-2 | Three Rivers Stadium (0-1) | 3-4 | |
| » W: Bob Walk (1-1) L: Danny Jackson (0-2) S: Roger Mason (2) | Fifth | 2 out |
| Wednesday, April 15 |
| » Lost to Pirates (6-2), 7-2 | Three Rivers Stadium (0-2) | 3-5 | Lost 2 |
| » W: Randy Tomlin (2-0) L: Mike Morgan (0-2) | Sixth | 3 out |
| Saturday, April 18 |
| » Defeated Cardinals (5-6), 5-4 | Busch Stadium II (1-0) | 4-5 | |
| » W: Shawn Boskie (2-0) L: Omar Olivares (1-2) S: Chuck McElroy (3) | Fourth | 3½ out |
| Sunday, April 19 |
| » Lost to Cardinals (6-6), 4-3 | Busch Stadium II (1-1) | 4-6 | |
| » W: Jose DeLeon (1-1) L: Danny Jackson (0-3) S: Lee Smith (4) | Fourth | 4½ out |
| Monday, April 20 |
| » Defeated Phillies (4-9), 8-3 | Wrigley Field (3-1) | 5-6 | |
| » W: Greg Maddux (3-0) L: Kyle Abbott (0-3) | Fourth | 4½ out |
| Tuesday, April 21 |
| » Lost to Phillies (5-9), 7-5 | Wrigley Field (3-2) | 5-7 | |
| » W: Mitch Williams (1-0) L: Heathcliff Slocumb (0-1) S: Curt Schilling (1) | Fifth | 5½ out |
| Wednesday, April 22 |
| » Defeated Phillies (5-10), 9-5 | Wrigley Field (4-2) | 6-7 | |
| » W: Shawn Boskie (3-0) L: Terry Mulholland (0-3) | Third | 5½ out |
| Thursday, April 23 |
| » Lost to Phillies (6-10), 8-2 | Wrigley Field (4-3) | 6-8 | |
| » W: Tommy Greene (2-1) L: Frank Castillo (0-1) | Fourth | 5½ out |
| Friday, April 24 |
| » Lost to Pirates (13-3), 3-2 | Wrigley Field (4-4) | 6-9 | Lost 2 |
| » W: Roger Mason (1-0) L: Bob Scanlan (0-1) S: Stan Belinda (4) | Fifth | 6½ out |
| Saturday, April 25 |
| » Lost to Pirates (14-3), 1-0 | Wrigley Field (4-5) | 6-10 | Lost 3 |
| » W: Randy Tomlin (4-0) L: Greg Maddux (3-1) S: Stan Belinda (5) | Fifth | 7½ out |
| Sunday, April 26 |
| » Defeated Pirates (14-4), 5-4 | Wrigley Field (5-5) | 7-10 | |
| » W: Chuck McElroy (1-0) L: Roger Mason (1-1) | Fifth | 6½ out |
| Monday, April 27 |
| » Lost to Braves (9-11), 5-0 | Atlanta-Fulton County Stadium (0-1) | 7-11 | |
| » W: Tom Glavine (3-1) L: Shawn Boskie (3-1) | Sixth | 7 out |
| Tuesday, April 28 |
| » Lost to Braves (10-11), 1-0 | Atlanta-Fulton County Stadium (0-2) | 7-12 | Lost 2 |
| » W: Charlie Leibrandt (2-1) L: Frank Castillo (0-2) S: Alejandro Pena (3) | Sixth | 7 out |
| Wednesday, April 29 |
| » Lost to Braves (11-11), 8-0 | Atlanta-Fulton County Stadium (0-3) | 7-13 | Lost 3 |
| » W: John Smoltz (2-2) L: Danny Jackson (0-4) | Sixth | 8 out |
| Friday, May 1 |
| » Lost to Reds (12-10), 4-0 | Riverfront Stadium (0-1) | 7-14 | Lost 4 |
| » W: Greg Swindell (2-1) L: Greg Maddux (3-2) S: Rob Dibble (3) | Sixth | 8 out |
| Saturday, May 2 |
| » Defeated Reds (12-11), 10-3 | Riverfront Stadium (1-1) | 8-14 | |
| » W: Mike Morgan (1-2) L: Chris Hammond (2-2) | Sixth | 8 out |
| Sunday, May 3 |
| » Lost to Reds (13-11), 7-1 | Riverfront Stadium (1-2) | 8-15 | |
| » W: Scott Bankhead (3-0) L: Shawn Boskie (3-2) | Sixth | 8 out |
| Monday, May 4 |
| » Lost to Braves (13-13), 6-1 | Wrigley Field (5-6) | 8-16 | Lost 2 |
| » W: John Smoltz (3-2) L: Frank Castillo (0-3) | Sixth | 9 out |
| Tuesday, May 5 |
| » Defeated Braves (13-14), 4-3 | Wrigley Field (6-6) | 9-16 | |
| » W: Chuck McElroy (2-0) L: Alejandro Pena (0-2) | Sixth | 9 out |
| Wednesday, May 6 |
| » Defeated Astros (13-14), 8-4 | Wrigley Field (7-6) | 10-16 | Won 2 |
| » W: Greg Maddux (4-2) L: Pete Harnisch (2-4) | Sixth | 9 out |
| Thursday, May 7 |
| » Defeated Astros (13-15), 9-2 | Wrigley Field (8-6) | 11-16 | Won 3 |
| » W: Mike Morgan (2-2) L: Ryan Bowen (0-4) | Sixth | 8 out |
| Friday, May 8 |
| » Lost to Reds (16-13), 10-7 | Wrigley Field (8-7) | 11-17 | |
| » W: Norm Charlton (1-0) L: Chuck McElroy (2-1) | Sixth | 9 out |
| Saturday, May 9 |
| » Defeated Reds (16-14), 3-1 | Wrigley Field (9-7) | 12-17 | |
| » W: Frank Castillo (1-3) L: Tom Browning (3-2) S: Paul Assenmacher (1) | Sixth | 9 out |
| Sunday, May 10 |
| » Lost to Reds (17-14), 6-0 | Wrigley Field (9-8) | 12-18 | |
| » W: Tim Belcher (2-4) L: Danny Jackson (0-5) | Sixth | 9 out |
| Monday, May 11 |
| » Lost to Astros (15-17), 2-1 | Astrodome (0-1) | 12-19 | Lost 2 |
| » W: Xavier Hernandez (3-0) L: Chuck McElroy (2-2) | Sixth | 9½ out |
| Tuesday, May 12 |
| » Defeated Astros (15-18), 3-2 | Astrodome (1-1) | 13-19 | |
| » W: Paul Assenmacher (1-1) L: Joe Boever (0-1) | Sixth | 8½ out |
| » Major-league debuts: Alex Arias (Cubs) |
| Wednesday, May 13 |
| » Defeated Astros (15-19), 8-3 | Astrodome (2-1) | 14-19 | Won 2 |
| » W: Shawn Boskie (4-2) L: Butch Henry (0-3) | Fifth | 8½ out |
| Friday, May 15 |
| » Defeated Giants (19-15), 5-3 | Candlestick Park (1-0) | 15-19 | Won 3 |
| » W: Bob Scanlan (1-1) L: Jeff Brantley (2-1) S: Paul Assenmacher (2) | Fourth | 8 out |
| Saturday, May 16 |
| » Lost to Giants (20-15), 2-0 | Candlestick Park (1-1) | 15-20 | |
| » W: John Burkett (3-1) L: Greg Maddux (4-3) S: Rod Beck (2) | Fifth | 8 out |
| Sunday, May 17 |
| » Defeated Giants (20-16), 4-3 | Candlestick Park (2-1) | 16-20 | |
| » W: Mike Morgan (3-2) L: Dave Burba (2-4) S: Bob Scanlan (1) | Fifth | 7 out |
| Monday, May 18 |
| » Defeated Dodgers (13-21), 3-0 | Dodger Stadium (1-0) | 17-20 | Won 2 |
| » W: Frank Castillo (2-3) L: Kevin Gross (1-4) S: Chuck McElroy (4) | Fourth | 6½ out |
| Tuesday, May 19 |
| » Lost to Dodgers (14-21), 5-2 | Dodger Stadium (1-1) | 17-21 | |
| » W: Orel Hershiser (3-3) L: Shawn Boskie (4-3) S: Roger McDowell (5) | Fourth | 6½ out |
| Wednesday, May 20 |
| » Lost to Dodgers (15-21), 5-3 | Dodger Stadium (1-2) | 17-22 | Lost 2 |
| » W: Bob Ojeda (2-3) L: Danny Jackson (0-6) S: John Candelaria (1) | Sixth | 6½ out |
| Friday, May 22 |
| » Lost to Padres (23-19), 2-0 | San Diego/Jack Murphy Stadium (0-1) | 17-23 | Lost 3 |
| » W: Andy Benes (5-3) L: Greg Maddux (4-4) | Sixth | 7 out |
| Saturday, May 23 |
| » Defeated Padres (23-20), 7-2 | San Diego/Jack Murphy Stadium (1-1) | 18-23 | |
| » W: Mike Morgan (4-2) L: Bruce Hurst (3-4) | Sixth | 6 out |
| Sunday, May 24 |
| » Defeated Padres (23-21), 6-4 | San Diego/Jack Murphy Stadium (2-1) | 19-23 | Won 2 |
| » W: Frank Castillo (3-3) L: Jose Melendez (4-3) S: Chuck McElroy (5) | Fifth | 5½ out |
| Tuesday, May 26 |
| » Lost to Giants (25-18), 3-2 | Wrigley Field (9-9) | 19-24 | |
| » W: Mike Jackson (1-1) L: Chuck McElroy (2-3) S: Jeff Brantley (5) | Sixth | 6 out |
| Wednesday, May 27 |
| » Lost to Giants (26-18), 6-2 | Wrigley Field (9-10) | 19-25 | Lost 2 |
| » W: John Burkett (5-1) L: Greg Maddux (4-5) | Sixth | 6 out |
| » Major-league debuts: Jim Bullinger (Cubs) |
| Thursday, May 28 |
| » Defeated Giants (26-19), 5-0 | Wrigley Field (10-10) | 20-25 | |
| » W: Mike Morgan (5-2) L: Dave Burba (2-6) | Sixth | 5½ out |
| Friday, May 29 |
| » Lost to Dodgers (20-23), 1-0 | Wrigley Field (10-11) | 20-26 | |
| » W: Ramon Martinez (3-1) L: Frank Castillo (3-4) | Sixth | 5½ out |
| Saturday, May 30 |
| » Lost to Dodgers (21-23), 3-2 | Wrigley Field (10-12) | 20-27 | Lost 2 |
| » W: Orel Hershiser (4-3) L: Ken Patterson (0-1) S: Roger McDowell (7) | Sixth | 6½ out |
| Sunday, May 31 |
| » Lost to Dodgers (22-23), 6-2 | Wrigley Field (10-13) | 20-28 | Lost 3 |
| » W: Kevin Gross (3-4) L: Danny Jackson (0-7) | Sixth | 6½ out |
| Monday, June 1 |
| » Defeated Padres (28-23), 6-1 | Wrigley Field (11-13) | 21-28 | |
| » W: Greg Maddux (5-5) L: Andy Benes (5-4) | Sixth | 6 out |
| » Major-league debuts: Dan Walters (Padres) |
| Tuesday, June 2 |
| » Defeated Padres (28-24), 3-2 | Wrigley Field (12-13) | 22-28 | Won 2 |
| » W: Shawn Boskie (5-3) L: Gene Harris (0-1) | Fifth | 5 out |
| » Major-league debuts: Frank Seminara (Padres) |
| Wednesday, June 3 |
| » Lost to Padres (29-24), 5-1 | Wrigley Field (12-14) | 22-29 | |
| » W: Bruce Hurst (5-4) L: Frank Castillo (3-5) | Fifth | 6 out |
| Friday, June 5 |
| » Defeated Expos (22-28), 10-4 | Stade Olympique (1-0) | 23-29 | |
| » W: Danny Jackson (1-7) L: Mark Gardner (3-5) S: Bob Scanlan (2) | Sixth | 7 out |
| » Lost to Expos (23-28), 6-2 | Stade Olympique (1-1) | 23-30 | |
| » W: Chris Nabholz (4-4) L: Greg Maddux (5-6) S: John Wetteland (9) | Sixth | 7 out |
| » Major-league debuts: Pete Young (Expos) |
| Sunday, June 7 |
| » Lost to Expos (24-28), 3-2 | Stade Olympique (1-2) | 23-31 | Lost 2 |
| » W: Jeff Fassero (3-2) L: Bob Scanlan (1-2) | Sixth | 7½ out |
| Monday, June 8 |
| » Defeated Cardinals (28-27), 5-2 | Busch Stadium II (2-1) | 24-31 | |
| » W: Jeff Robinson (1-0) L: Juan Agosto (2-4) S: Bob Scanlan (3) | Fifth | 6 out |
| » Defeated Cardinals (28-28), 6-4 | Busch Stadium II (3-1) | 25-31 | Won 2 |
| » W: Frank Castillo (4-5) L: Jose DeLeon (2-6) S: Jim Bullinger (1) | Fifth | 6 out |
| Tuesday, June 9 |
| » Lost to Cardinals (29-28), 6-5 | Busch Stadium II (3-2) | 25-32 | |
| » W: Cris Carpenter (3-2) L: Bob Scanlan (1-3) | Fifth | 7 out |
| Wednesday, June 10 |
| » Defeated Cardinals (29-29), 4-2 | Busch Stadium II (4-2) | 26-32 | |
| » W: Greg Maddux (6-6) L: Mark Clark (0-1) S: Jim Bullinger (2) | Fifth | 7 out |
| Friday, June 12 |
| » Defeated Expos (26-30), 5-2 | Wrigley Field (13-14) | 27-32 | Won 2 |
| » W: Chuck McElroy (3-3) L: Dennis Martinez (6-5) S: Jim Bullinger (3) | Fifth | 7 out |
| Saturday, June 13 |
| » Defeated Expos (26-31), 4-3 | Wrigley Field (14-14) | 28-32 | Won 3 |
| » W: Frank Castillo (5-5) L: Chris Nabholz (4-5) S: Jim Bullinger (4) | Fourth | 7 out |
| Sunday, June 14 |
| » Defeated Expos (26-32), 5-1 | Wrigley Field (15-14) | 29-32 | Won 4 |
| » W: Danny Jackson (2-7) L: Ken Hill (5-4) | Third | 7 out |
| Monday, June 15 |
| » Defeated Cardinals (31-31), 7-1 | Wrigley Field (16-14) | 30-32 | Won 5 |
| » W: Greg Maddux (7-6) L: Bob Tewksbury (6-2) | Third | 6 out |
| Tuesday, June 16 |
| » Defeated Cardinals (31-32), 2-1 | Wrigley Field (17-14) | 31-32 | Won 6 |
| » W: Bob Scanlan (2-3) L: Mark Clark (0-2) S: Jim Bullinger (5) | Second | 6 out |
| Thursday, June 18 |
| » Lost to Phillies (29-34), 4-3 | Veteran's Stadium (1-3) | 31-33 | |
| » W: Mike Hartley (3-1) L: Bob Scanlan (2-4) S: Mitch Williams (13) | Third | 6½ out |
| Friday, June 19 |
| » Defeated Phillies (29-35), 5-2 | Veteran's Stadium (2-3) | 32-33 | |
| » W: Danny Jackson (3-7) L: Brad Brink (0-3) S: Jim Bullinger (6) | Second | 5½ out |
| Saturday, June 20 |
| » Lost to Phillies (30-35), 4-1 | Veteran's Stadium (2-4) | 32-34 | |
| » W: Terry Mulholland (7-4) L: Greg Maddux (7-7) S: Mitch Williams (14) | Third | 5½ out |
| Sunday, June 21 |
| » Defeated Phillies (30-36), 5-2 | Veteran's Stadium (3-4) | 33-34 | |
| » W: Mike Morgan (6-2) L: Kyle Abbott (0-8) S: Paul Assenmacher (3) | Second | 5½ out |
| Monday, June 22 |
| » Lost to Mets (33-36), 8-2 | Shea Stadium (0-1) | 33-35 | |
| » W: Sid Fernandez (6-7) L: Shawn Boskie (5-4) | Second | 6½ out |
| Tuesday, June 23 |
| » Lost to Mets (34-36), 4-1 | Shea Stadium (0-2) | 33-36 | Lost 2 |
| » W: Pete Schourek (1-3) L: Frank Castillo (5-6) S: John Franco (10) | Third | 7½ out |
| Wednesday, June 24 |
| » Lost to Mets (35-36), 3-2 | Shea Stadium (0-3) | 33-37 | Lost 3 |
| » W: Dwight Gooden (5-6) L: Danny Jackson (3-8) S: John Franco (11) | Fifth | 7½ out |
| Thursday, June 25 |
| » Defeated Mets (35-37), 9-2 | Shea Stadium (1-3) | 34-37 | |
| » W: Greg Maddux (8-7) L: Anthony Young (2-7) | Fourth | 7 out |
| Friday, June 26 |
| » Defeated Phillies (32-38), 3-0 | Wrigley Field (18-14) | 35-37 | Won 2 |
| » W: Mike Morgan (7-2) L: Kyle Abbott (0-9) S: Jim Bullinger (7) | Third | 6 out |
| Saturday, June 27 |
| » Lost to Phillies (33-38), 5-4 | Wrigley Field (18-15) | 35-38 | |
| » W: Mike Hartley (4-1) L: Chuck McElroy (3-4) S: Mitch Williams (16) | Fourth | 7 out |
| Sunday, June 28 |
| » Defeated Phillies (33-39), 5-3 | Wrigley Field (19-15) | 36-38 | |
| » W: Frank Castillo (6-6) L: Curt Schilling (6-5) S: Paul Assenmacher (4) | Third | 6 out |
| Monday, June 29 |
| » Defeated Mets (36-40), 5-2 | Wrigley Field (20-15) | 37-38 | Won 2 |
| » W: Danny Jackson (4-8) L: Dwight Gooden (5-7) S: Paul Assenmacher (5) | Third | 5 out |
| Tuesday, June 30 |
| » Defeated Mets (36-41), 3-1 | Wrigley Field (21-15) | 38-38 | Won 3 |
| » W: Greg Maddux (9-7) L: Anthony Young (2-8) | Second | 5 out |
| Wednesday, July 1 |
| » Lost to Mets (37-41), 6-4 | Wrigley Field (21-16) | 38-39 | |
| » W: Lee Guetterman (2-1) L: Jim Bullinger (0-1) S: Anthony Young (1) | Second | 6 out |
| Friday, July 3 |
| » Lost to Braves (43-34), 3-0 | Atlanta-Fulton County Stadium (0-4) | 38-40 | Lost 2 |
| » W: Tom Glavine (12-3) L: Shawn Boskie (5-5) | Third | 5½ out |
| Saturday, July 4 |
| » Lost to Braves (44-34), 4-2 | Atlanta-Fulton County Stadium (0-5) | 38-41 | Lost 3 |
| » W: Charlie Leibrandt (7-3) L: Danny Jackson (4-9) S: Kent Mercker (3) | Fourth | 5½ out |
| Sunday, July 5 |
| » Defeated Braves (44-35), 8-0 | Atlanta-Fulton County Stadium (1-5) | 39-41 | |
| » W: Greg Maddux (10-7) L: John Smoltz (9-6) | Third | 4½ out |
| Monday, July 6 |
| » Lost to Reds (49-31), 6-2 | Wrigley Field (21-17) | 39-42 | |
| » W: Scott Ruskin (3-1) L: Mike Morgan (7-3) S: Rob Dibble (12) | Fourth | 5½ out |
| Tuesday, July 7 |
| » Lost to Reds (50-31), 3-2 | Wrigley Field (21-18) | 39-43 | Lost 2 |
| » W: Jose Rijo (6-6) L: Frank Castillo (6-7) S: Norm Charlton (20) | Fourth | 6½ out |
| Wednesday, July 8 |
| » Defeated Reds (50-32), 3-2 | Wrigley Field (22-18) | 40-43 | |
| » W: Paul Assenmacher (2-1) L: Rob Dibble (0-4) | Fourth | 5½ out |
| Thursday, July 9 |
| » Lost to Braves (46-37), 2-0 | Wrigley Field (22-19) | 40-44 | |
| » W: Mike Stanton (2-4) L: Jim Bullinger (0-2) S: Alejandro Pena (5) | Fourth | 5½ out |
| Friday, July 10 |
| » Lost to Braves (47-37), 4-0 | Wrigley Field (22-20) | 40-45 | Lost 2 |
| » W: John Smoltz (10-6) L: Greg Maddux (10-8) | Fifth | 6½ out |
| Saturday, July 11 |
| » Lost to Braves (48-37), 3-1 | Wrigley Field (22-21) | 40-46 | Lost 3 |
| » W: Steve Avery (7-7) L: Bob Scanlan (2-5) S: Alejandro Pena (6) | Fifth | 7½ out |
| Sunday, July 12 |
| » Lost to Braves (49-37), 7-4 | Wrigley Field (22-22) | 40-47 | Lost 4 |
| » W: Kent Mercker (3-0) L: Paul Assenmacher (2-2) S: Alejandro Pena (7) | Fifth | 8½ out |
| Thursday, July 16 |
| » Lost to Pirates (50-39), 2-1 | Three Rivers Stadium (0-3) | 40-48 | Lost 5 |
| » W: Doug Drabek (8-7) L: Shawn Boskie (5-6) S: Stan Belinda (14) | Fifth | 9½ out |
| Friday, July 17 |
| » Defeated Pirates (50-40), 2-1 | Three Rivers Stadium (1-3) | 41-48 | |
| » W: Greg Maddux (11-8) L: Randy Tomlin (10-6) S: Bob Scanlan (4) | Fifth | 8½ out |
| Saturday, July 18 |
| » Lost to Pirates (51-40), 4-0 | Three Rivers Stadium (1-4) | 41-49 | |
| » W: Bob Walk (3-3) L: Mike Morgan (7-4) S: Bob Patterson (5) | Fifth | 9½ out |
| Sunday, July 19 |
| » Defeated Pirates (51-41), 4-2 | Three Rivers Stadium (2-4) | 42-49 | |
| » W: Bob Scanlan (3-5) L: Denny Neagle (3-5) | Fifth | 8½ out |
| Monday, July 20 |
| » Lost to Reds (55-36), 5-2 | Riverfront Stadium (1-3) | 42-50 | |
| » W: Scott Ruskin (4-1) L: Chuck McElroy (3-5) S: Rob Dibble (13) | Fifth | 8½ out |
| Tuesday, July 21 |
| » Defeated Reds (55-37), 1-0 | Riverfront Stadium (2-3) | 43-50 | |
| » W: Ken Patterson (1-1) L: Tim Belcher (8-9) S: Bob Scanlan (5) | Fifth | 7½ out |
| Wednesday, July 22 |
| » Defeated Reds (55-38), 3-0 | Riverfront Stadium (3-3) | 44-50 | Won 2 |
| » W: Greg Maddux (12-8) L: Greg Swindell (9-3) | Fifth | 7½ out |
| Friday, July 24 |
| » Defeated Astros (43-53), 1-0 | Astrodome (3-1) | 45-50 | Won 3 |
| » W: Mike Morgan (8-4) L: Doug Jones (7-7) S: Bob Scanlan (6) | Fifth | 6½ out |
| Saturday, July 25 |
| » Lost to Astros (44-53), 3-2 | Astrodome (3-2) | 45-51 | |
| » W: Xavier Hernandez (6-1) L: Chuck McElroy (3-6) | Fifth | 6½ out |
| Sunday, July 26 |
| » Defeated Astros (44-54), 8-5 | Astrodome (4-2) | 46-51 | |
| » W: Mike Harkey (1-0) L: Shane Reynolds (0-1) | Fifth | 6½ out |
| Monday, July 27 |
| » Defeated Pirates (53-46), 3-2 | Wrigley Field (23-22) | 47-51 | Won 2 |
| » W: Greg Maddux (13-8) L: Doug Drabek (8-8) S: Jeff Robinson (1) | Fourth | 5½ out |
| Tuesday, July 28 |
| » Defeated Pirates (53-47), 11-1 | Wrigley Field (24-22) | 48-51 | Won 3 |
| » W: Mike Morgan (9-4) L: Randy Tomlin (10-7) | Third | 4½ out |
| » Major-league debuts: Steve Cooke Al Martin and Blas Minor (Pirates) |
| Wednesday, July 29 |
| » Defeated Pirates (53-48), 6-4 | Wrigley Field (25-22) | 49-51 | Won 4 |
| » W: Paul Assenmacher (3-2) L: Stan Belinda (5-3) | Second | 3½ out |
| Saturday, August 1 |
| » Lost to Mets (50-52), 3-0 | Shea Stadium (1-4) | 49-52 | |
| » W: Pete Schourek (3-4) L: Greg Maddux (13-9) S: Anthony Young (8) | Third | 5 out |
| » Defeated Mets (50-53), 6-1 | Shea Stadium (2-4) | 50-52 | |
| » W: Jeff Robinson (2-0) L: Wally Whitehurst (1-6) | Third | 5 out |
| Sunday, August 2 |
| » Lost to Mets (51-53), 4-2 | Shea Stadium (2-5) | 50-53 | |
| » W: David Cone (13-4) L: Mike Morgan (9-5) S: John Franco (12) | Fourth | 6 out |
| Monday, August 3 |
| » Lost to Expos (56-50), 3-2 | Stade Olympique (1-3) | 50-54 | Lost 2 |
| » W: Dennis Martinez (11-10) L: Frank Castillo (6-8) S: John Wetteland (24) | Fourth | 6½ out |
| Tuesday, August 4 |
| » Defeated Expos (56-51), 8-6 | Stade Olympique (2-3) | 51-54 | |
| » W: Chuck McElroy (4-6) L: Bill Sampen (0-4) S: Paul Assenmacher (6) | Third | 6½ out |
| Wednesday, August 5 |
| » Lost to Expos (57-51), 5-3 | Stade Olympique (2-4) | 51-55 | |
| » W: Brian Barnes (3-3) L: Ken Patterson (1-2) S: John Wetteland (25) | Third | 7½ out |
| Thursday, August 6 |
| » Defeated Mets (51-56), 5-2 | Wrigley Field (26-22) | 52-55 | |
| » W: Greg Maddux (14-9) L: Wally Whitehurst (1-7) | Third | 7½ out |
| Friday, August 7 |
| » Defeated Mets (51-57), 9-1 | Wrigley Field (27-22) | 53-55 | Won 2 |
| » W: Mike Morgan (10-5) L: David Cone (13-5) | Third | 7½ out |
| Saturday, August 8 |
| » Defeated Mets (51-58), 4-3 | Wrigley Field (28-22) | 54-55 | Won 3 |
| » W: Jim Bullinger (1-2) L: Lee Guetterman (3-2) | Third | 7½ out |
| Sunday, August 9 |
| » Defeated Mets (51-59), 6-2 | Wrigley Field (29-22) | 55-55 | Won 4 |
| » W: Mike Harkey (2-0) L: Sid Fernandez (9-9) | Third | 7½ out |
| Monday, August 10 |
| » Lost to Expos (61-52), 11-0 | Wrigley Field (29-23) | 55-56 | |
| » W: Brian Barnes (4-3) L: Jeff Robinson (2-1) | Third | 8½ out |
| Tuesday, August 11 |
| » Lost to Expos (62-52), 3-2 | Wrigley Field (29-24) | 55-57 | Lost 2 |
| » W: Bill Sampen (1-4) L: Jeff Robinson (2-2) | Third | 8½ out |
| Wednesday, August 12 |
| » Lost to Expos (63-52), 3-1 | Wrigley Field (29-25) | 55-58 | Lost 3 |
| » W: Chris Nabholz (8-8) L: Mike Morgan (10-6) S: Mel Rojas (9) | Third | 9½ out |
| Thursday, August 13 |
| » Lost to Astros (51-64), 4-3 | Wrigley Field (29-26) | 55-59 | Lost 4 |
| » W: Jimmy Jones (5-5) L: Frank Castillo (6-9) S: Doug Jones (26) | Third | 10 out |
| Friday, August 14 |
| » Defeated Astros (51-65), 4-2 | Wrigley Field (30-26) | 56-59 | |
| » W: Mike Harkey (3-0) L: Darryl Kile (2-7) S: Paul Assenmacher (7) | Third | 9 out |
| Saturday, August 15 |
| » Lost to Astros (52-65), 5-0 | Wrigley Field (30-27) | 56-60 | |
| » W: Butch Henry (4-8) L: Jim Bullinger (1-3) | Third | 9 out |
| Sunday, August 16 |
| » Defeated Astros (52-66), 1-0 | Wrigley Field (31-27) | 57-60 | |
| » W: Greg Maddux (15-9) L: Brian Williams (4-4) | Third | 9 out |
| Tuesday, August 18 |
| » Defeated Giants (56-63), 4-1 | Candlestick Park (3-1) | 58-60 | Won 2 |
| » W: Mike Morgan (11-6) L: Bud Black (9-6) | Third | 8½ out |
| Wednesday, August 19 |
| » Lost to Giants (57-63), 9-1 | Candlestick Park (3-2) | 58-61 | |
| » W: Bill Swift (9-3) L: Frank Castillo (6-10) | Third | 9½ out |
| Thursday, August 20 |
| » Defeated Giants (57-64), 6-5 | Candlestick Park (4-2) | 59-61 | |
| » W: Mike Harkey (4-0) L: Trevor Wilson (8-12) S: Bob Scanlan (7) | Third | 9½ out |
| Friday, August 21 |
| » Defeated Dodgers (52-70), 3-2 | Dodger Stadium (2-2) | 60-61 | Won 2 |
| » W: Jeff Robinson (3-2) L: Jay Howell (1-3) S: Bob Scanlan (8) | Third | 8½ out |
| Saturday, August 22 |
| » Defeated Dodgers (52-71), 5-4 | Dodger Stadium (3-2) | 61-61 | Won 3 |
| » W: Ken Patterson (2-2) L: John Candelaria (2-4) S: Bob Scanlan (9) | Third | 8½ out |
| Sunday, August 23 |
| » Defeated Dodgers (52-72), 4-2 | Dodger Stadium (4-2) | 62-61 | Won 4 |
| » W: Mike Morgan (12-6) L: Pedro Astacio (2-2) S: Chuck McElroy (6) | Third | 7½ out |
| Monday, August 24 |
| » Defeated Padres (66-58), 6-3 | San Diego/Jack Murphy Stadium (3-1) | 63-61 | Won 5 |
| » W: Frank Castillo (7-10) L: Greg Harris (2-5) S: Bob Scanlan (10) | Third | 6½ out |
| Tuesday, August 25 |
| » Lost to Padres (67-58), 7-4 | San Diego/Jack Murphy Stadium (3-2) | 63-62 | |
| » W: Mike Maddux (1-1) L: Ken Patterson (2-3) S: Randy Myers (28) | Third | 7½ out |
| Wednesday, August 26 |
| » Lost to Padres (68-58), 3-0 | San Diego/Jack Murphy Stadium (3-3) | 63-63 | Lost 2 |
| » W: Craig Lefferts (13-8) L: Greg Maddux (15-10) S: Randy Myers (29) | Third | 8½ out |
| Friday, August 28 |
| » Defeated Giants (59-69), 3-2 | Wrigley Field (32-27) | 64-63 | |
| » W: Mike Morgan (13-6) L: Mike Jackson (5-5) S: Bob Scanlan (11) | Third | 7½ out |
| Saturday, August 29 |
| » Defeated Giants (59-70), 7-2 | Wrigley Field (33-27) | 65-63 | Won 2 |
| » W: Frank Castillo (8-10) L: Dave Burba (2-7) S: Bob Scanlan (12) | Third | 7½ out |
| » Major-league debuts: Steve Hosey (Giants) |
| Sunday, August 30 |
| » Defeated Giants (59-71), 3-1 | Wrigley Field (34-27) | 66-63 | Won 3 |
| » W: Jim Bullinger (2-3) L: Trevor Wilson (8-14) | Third | 7½ out |
| » Major-league debuts: Steve Reed (Giants) |
| Monday, August 31 |
| » Defeated Dodgers (53-78), 2-0 | Wrigley Field (35-27) | 67-63 | Won 4 |
| » W: Greg Maddux (16-10) L: Tom Candiotti (9-12) | Third | 7 out |
| Tuesday, September 1 |
| » Lost to Dodgers (54-78), 5-4 | Wrigley Field (35-28) | 67-64 | |
| » W: Roger McDowell (6-8) L: Heathcliff Slocumb (0-2) S: John Candelaria (5) | Third | 8 out |
| » Major-league debuts: Billy Ashley Rafael Bournigal and Mike Piazza (Dodgers) |
| Wednesday, September 2 |
| » Defeated Dodgers (54-79), 5-1 | Wrigley Field (36-28) | 68-64 | |
| » W: Mike Morgan (14-6) L: Bob Ojeda (6-7) | Third | 8 out |
| Friday, September 4 |
| » Lost to Padres (71-62), 7-5 | Wrigley Field (36-29) | 68-65 | |
| » W: Jeremy Hernandez (1-1) L: Shawn Boskie (5-7) | Third | 9½ out |
| Saturday, September 5 |
| » Lost to Padres (72-62), 5-3 | Wrigley Field (36-30) | 68-66 | Lost 2 |
| » W: Jose Melendez (6-7) L: Greg Maddux (16-11) S: Randy Myers (31) | Third | 10½ out |
| Former Cub Billy Herman dies in W.Palm Beach, FL at the age of 84. |
| Sunday, September 6 |
| » Lost to Padres (73-62), 3-1 | Wrigley Field (36-31) | 68-67 | Lost 3 |
| » W: Andy Benes (11-12) L: Jim Bullinger (2-4) S: Randy Myers (32) | Third | 10½ out |
| Monday, September 7 |
| » Defeated Pirates (79-58), 6-5 | Three Rivers Stadium (3-4) | 69-67 | |
| » W: Paul Assenmacher (4-2) L: Stan Belinda (5-4) S: Bob Scanlan (13) | Third | 9½ out |
| » Major-league debuts: Fernando Ramsey (Cubs) |
| Tuesday, September 8 |
| » Lost to Pirates (80-58), 5-2 | Three Rivers Stadium (3-5) | 69-68 | |
| » W: Doug Drabek (12-10) L: Shawn Boskie (5-8) | Third | 10½ out |
| Wednesday, September 9 |
| » Lost to Pirates (81-58), 13-8 | Three Rivers Stadium (3-6) | 69-69 | Lost 2 |
| » W: Danny Cox (4-3) L: Jeff Robinson (3-3) | Fourth | 11½ out |
| Friday, September 11 |
| » Defeated Cardinals (69-69), 8-2 | Busch Stadium II (5-2) | 70-69 | |
| » W: Greg Maddux (17-11) L: Omar Olivares (8-9) | Third | 10½ out |
| Saturday, September 12 |
| » Lost to Cardinals (70-69), 11-3 | Busch Stadium II (5-3) | 70-70 | |
| » W: Rheal Cormier (7-10) L: Mike Morgan (14-7) | Fourth | 11½ out |
| » Major-league debuts: Jeff Hartsock (Cubs) |
| Sunday, September 13 |
| » Lost to Cardinals (71-69), 10-3 | Busch Stadium II (5-4) | 70-71 | Lost 2 |
| » W: Bob Tewksbury (16-5) L: Jim Bullinger (2-5) | Fourth | 11½ out |
| Monday, September 14 |
| » Lost to Mets (64-78), 10-8 | Wrigley Field (36-32) | 70-72 | Lost 3 |
| » W: Jeff Innis (6-8) L: Chuck McElroy (4-7) S: Anthony Young (14) | Fourth | 12½ out |
| Tuesday, September 15 |
| » Lost to Mets (65-78), 4-2 | Wrigley Field (36-33) | 70-73 | Lost 4 |
| » W: Mark Dewey (1-0) L: Shawn Boskie (5-9) | Fourth | 13½ out |
| Wednesday, September 16 |
| » Defeated Phillies (59-84), 14-9 | Wrigley Field (37-33) | 71-73 | |
| » W: Greg Maddux (18-11) L: Ben Rivera (5-4) | Fourth | 12½ out |
| Thursday, September 17 |
| » Defeated Phillies (59-85), 3-0 | Wrigley Field (38-33) | 72-73 | Won 2 |
| » W: Mike Morgan (15-7) L: Jose DeLeon (2-8) | Fourth | 12½ out |
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