| Thursday, February 13 |
| Former Cub Ken Hubbs dies in Provo, UT at the age of 23. |
| Monday, February 17 |
| Future Cub Mike Campbell is born in Seattle, WA. |
| Tuesday, February 18 |
| Future Cub Kevin Tapani is born in Des Moines, IA. |
| Wednesday, April 8 |
| Former Cub George Moriarty dies in Miami, FL at the age of 80. |
| Thursday, April 9 |
| Future Cub Blaise Ilsley is born in Alpena, MI. |
| Monday, April 13 |
| » Major-league debuts: Bobby Knoop (Angels) |
| Future Cub Doug Strange is born in Greenville, SC. |
| Tuesday, April 14 |
| » Defeated Pirates (0-1), 8-4 | Forbes Field (1-0) | 1-0 | |
| » Starters: Larry Jackson vs Bob Veale | First | -- |
| Wednesday, April 15 |
| » Lost to Pirates (1-1), 5-4 | Forbes Field (1-1) | 1-1 | |
| » Starters: Fred Norman vs Joe Gibbon | Third | 1 out |
| Friday, April 17 |
| » Lost to Phillies (3-0), 10-8 | Wrigley Field (0-1) | 1-2 | Lost 2 |
| » Starters: Art Mahaffey vs Dick Ellsworth | Fifth | 2 out |
| » Major-league debuts: Johnny Briggs (Cubs) |
| Saturday, April 18 |
| » Defeated Phillies (3-1), 7-0 | Wrigley Field (1-1) | 2-2 | |
| » Starters: Ray Culp vs Bob Buhl | Third | 1 out |
| » Major-league debuts: Rick Wise (Phillies) |
| Sunday, April 19 |
| » Lost to Phillies (4-1), 8-1 | Wrigley Field (1-2) | 2-3 | |
| » Starters: Dennis Bennett vs Larry Jackson | Fifth | 2 out |
| » Major-league debuts: Paul Popovich (Cubs) |
| Tuesday, April 21 |
| » Lost to Pirates (4-2), 8-5 | Wrigley Field (1-3) | 2-4 | Lost 2 |
| » Starters: Vern Law vs Fred Norman | Sixth | 2½ out |
| Thursday, April 23 |
| » Defeated Mets (1-5), 5-1 | Shea Stadium (1-0) | 3-4 | |
| » Starters: Dick Ellsworth vs Tracy Stallard | Seventh | 2½ out |
| Friday, April 24 |
| » Lost to Phillies (6-1), 10-0 | Shibe Park (0-1) | 3-5 | |
| » Starters: Bob Buhl vs Jim Bunning | Eighth | 3½ out |
| Saturday, April 25 |
| » Defeated Phillies (6-2), 4-1 | Shibe Park (1-1) | 4-5 | |
| » Starters: Larry Jackson vs Dennis Bennett | Seventh | 2½ out |
| Sunday, April 26 |
| » Lost to Phillies (7-2), 5-1 | Shibe Park (1-2) | 4-6 | |
| » Starters: Fred Norman vs Ray Culp | Sixth | 3½ out |
| Wednesday, April 29 |
| » Lost to Giants (8-3), 4-0 | Wrigley Field (1-4) | 4-7 | Lost 2 |
| » Starters: Juan Marichal vs Dick Ellsworth | Eighth | 4½ out |
| Friday, May 1 |
| » Defeated Astros (7-10), 11-3 | Colt Stadium (1-0) | 5-7 | |
| » Starters: Larry Jackson vs Bob Bruce | Sixth | 5 out |
| Saturday, May 2 |
| » Defeated Astros (7-11), 9-0 | Colt Stadium (2-0) | 6-7 | Won 2 |
| » Starters: Bob Buhl vs Jim Owens | Seventh | 4 out |
| Sunday, May 3 |
| » Lost to Astros (8-11), 5-3 | Colt Stadium (2-1) | 6-8 | |
| » Starters: Fred Norman vs Hal Brown | Fifth | 4 out |
| Monday, May 4 |
| » Lost to Dodgers (8-12), 2-1 | Dodger Stadium (0-1) | 6-9 | Lost 2 |
| » Starters: Dick Ellsworth vs Sandy Koufax | Seventh | 5 out |
| Wednesday, May 6 |
| » Defeated Giants (12-5), 4-2 | Candlestick Park (1-0) | 7-9 | |
| » Starters: Larry Jackson vs Bob Hendley | Sixth | 4½ out |
| Thursday, May 7 |
| » Lost to Giants (13-5), 7-6 | Candlestick Park (1-1) | 7-10 | |
| » Starters: Bob Buhl vs Billy O'Dell | Seventh | 5½ out |
| Saturday, May 9 |
| » Defeated Astros (9-15), 9-1 | Wrigley Field (2-4) | 8-10 | |
| » Starters: Ken Johnson vs Dick Ellsworth | Seventh | 6 out |
| Sunday, May 10 |
| » Defeated Astros (9-16), 4-3 | Wrigley Field (3-4) | 9-10 | Won 2 |
| » Starters: Don Nottebart vs Larry Jackson | Seventh | 5½ out |
| » Lost to Astros (10-16), 4-1 | Wrigley Field (3-5) | 9-11 | |
| » Starters: Jim Owens vs Glen Hobbie | Seventh | 5½ out |
| Former Cub George McConnell dies in Chattanooga, TN at the age of 87. |
| Tuesday, May 12 |
| » Defeated Dodgers (10-16), 3-2 | Wrigley Field (4-5) | 10-11 | |
| » Starters: Joe Moeller vs Bob Buhl | Seventh | 5 out |
| Thursday, May 14 |
| » Lost to Dodgers (11-16), 6-4 | Wrigley Field (4-6) | 10-12 | |
| » Starters: Sandy Koufax vs Dick Ellsworth | Seventh | 5 out |
| » Lost to Dodgers (12-16), 5-0 | Wrigley Field (4-7) | 10-13 | Lost 2 |
| » Starters: Don Drysdale vs Fred Norman | Seventh | 5 out |
| Friday, May 15 |
| » Lost to Reds (14-13), 10-5 | Wrigley Field (4-8) | 10-14 | Lost 3 |
| » Starters: Bob Purkey vs Larry Jackson | Eighth | 5½ out |
| Saturday, May 16 |
| » Lost to Reds (15-13), 5-2 | Wrigley Field (4-9) | 10-15 | Lost 4 |
| » Starters: Joe Nuxhall vs Glen Hobbie | Eighth | 6 out |
| Sunday, May 17 |
| » Defeated Reds (15-14), 5-4 | Wrigley Field (5-9) | 11-15 | |
| » Starters: Jim O'Toole vs Bob Buhl | Eighth | 7 out |
| » Lost to Reds (16-14), 7-1 | Wrigley Field (5-10) | 11-16 | |
| » Starters: Jim Maloney vs Paul Toth | Eighth | 7 out |
| Tuesday, May 19 |
| » Defeated Cardinals (19-14), 7-4 | Sportsman's Park III (1-0) | 12-16 | |
| » Starters: Dick Ellsworth vs Ernie Broglio | Seventh | 6½ out |
| Wednesday, May 20 |
| » Lost to Cardinals (20-14), 1-0 | Sportsman's Park III (1-1) | 12-17 | |
| » Starters: Larry Jackson vs Bob Gibson | Eighth | 6½ out |
| Thursday, May 21 |
| » Lost to Cardinals (21-14), 10-3 | Sportsman's Park III (1-2) | 12-18 | Lost 2 |
| » Starters: Glen Hobbie vs Ray Sadecki | Ninth | 7½ out |
| Friday, May 22 |
| » Defeated Reds (16-17), 9-1 | Crosley Field (1-0) | 13-18 | |
| » Starters: Bob Buhl vs Joe Nuxhall | Ninth | 7½ out |
| Saturday, May 23 |
| » Defeated Reds (16-18), 5-3 | Crosley Field (2-0) | 14-18 | Won 2 |
| » Starters: Dick Ellsworth vs Jim Maloney | Ninth | 6½ out |
| Sunday, May 24 |
| » Lost to Reds (17-18), 6-5 | Crosley Field (2-1) | 14-19 | |
| » Starters: Larry Jackson vs Jim O'Toole | Ninth | 7 out |
| » Lost to Reds (18-18), 12-4 | Crosley Field (2-2) | 14-20 | Lost 2 |
| » Starters: Paul Toth vs Sammy Ellis | Ninth | 7 out |
| Tuesday, May 26 |
| » Lost to Mets (12-28), 19-1 | Wrigley Field (5-11) | 14-21 | Lost 3 |
| » Starters: Jack Fisher vs Bob Buhl | Eighth | 7 out |
| Wednesday, May 27 |
| » Defeated Mets (12-29), 7-1 | Wrigley Field (6-11) | 15-21 | |
| » Starters: Al Jackson vs Dick Ellsworth | Eighth | 7 out |
| Thursday, May 28 |
| » Defeated Mets (12-30), 2-0 | Wrigley Field (7-11) | 16-21 | Won 2 |
| » Starters: Galen Cisco vs Larry Jackson | Ninth | 7 out |
| Friday, May 29 |
| » Lost to Braves (23-18), 6-5 | Wrigley Field (7-12) | 16-22 | |
| » Starters: Denny Lemaster vs Glen Hobbie | Eighth | 7 out |
| Saturday, May 30 |
| » Defeated Braves (23-19), 4-2 | Wrigley Field (8-12) | 17-22 | |
| » Starters: Bob Sadowski vs Bob Buhl | Eighth | 6½ out |
| » Defeated Braves (23-20), 2-0 | Wrigley Field (9-12) | 18-22 | Won 2 |
| » Starters: Tony Cloninger vs Sterling Slaughter | Eighth | 6½ out |
| Sunday, May 31 |
| » Defeated Braves (23-21), 4-3 | Wrigley Field (10-12) | 19-22 | Won 3 |
| » Starters: Hank Fischer vs Dick Ellsworth | Seventh | 6½ out |
| Former Cub Rabbit Warstler dies in N.Canton, OH at the age of 61. |
| Tuesday, June 2 |
| » Defeated Cardinals (25-21), 5-2 | Wrigley Field (11-12) | 20-22 | Won 4 |
| » Starters: Curt Simmons vs Larry Jackson | Seventh | 6½ out |
| Wednesday, June 3 |
| » Lost to Cardinals (26-21), 7-5 | Wrigley Field (11-13) | 20-23 | |
| » Starters: Ray Sadecki vs Bob Buhl | Sixth | 7½ out |
| Thursday, June 4 |
| » Defeated Cardinals (26-22), 2-1 | Wrigley Field (12-13) | 21-23 | |
| » Starters: Bob Gibson vs Dick Ellsworth | Seventh | 6½ out |
| Friday, June 5 |
| » Defeated Braves (24-24), 5-2 | County Stadium (1-0) | 22-23 | Won 2 |
| » Starters: Sterling Slaughter vs Hank Fischer | Seventh | 5½ out |
| Saturday, June 6 |
| » Lost to Braves (25-24), 6-5 | County Stadium (1-1) | 22-24 | |
| » Starters: Larry Jackson vs Warren Spahn | Seventh | 6 out |
| Sunday, June 7 |
| » Defeated Braves (25-25), 5-2 | County Stadium (2-1) | 23-24 | |
| » Starters: Bob Buhl vs Denny Lemaster | Seventh | 6 out |
| Tuesday, June 9 |
| » Lost to Mets (17-35), 6-5 | Shea Stadium (1-1) | 23-25 | |
| » Starters: Dick Ellsworth vs Al Jackson | Seventh | 5½ out |
| » Defeated Mets (17-36), 5-2 | Shea Stadium (2-1) | 24-25 | |
| » Starters: Lew Burdette vs Galen Cisco | Seventh | 5½ out |
| Wednesday, June 10 |
| » Lost to Mets (18-36), 8-3 | Shea Stadium (2-2) | 24-26 | |
| » Starters: Sterling Slaughter vs Jack Fisher | Seventh | 6 out |
| Thursday, June 11 |
| » Defeated Mets (18-37), 6-3 | Shea Stadium (3-2) | 25-26 | |
| » Starters: Larry Jackson vs Bill Wakefield | Seventh | 5 out |
| Friday, June 12 |
| » Defeated Pirates (28-26), 7-1 | Wrigley Field (13-13) | 26-26 | Won 2 |
| » Starters: Bob Veale vs Bob Buhl | Sixth | 4 out |
| Saturday, June 13 |
| » Lost to Pirates (29-26), 10-7 | Wrigley Field (13-14) | 26-27 | |
| » Starters: Vern Law vs Lew Burdette | Sixth | 5 out |
| Sunday, June 14 |
| » Defeated Pirates (29-27), 5-2 | Wrigley Field (14-14) | 27-27 | |
| » Starters: Steve Blass vs Dick Ellsworth | Sixth | 5½ out |
| Tuesday, June 16 |
| » Lost to Phillies (33-21), 4-2 | Wrigley Field (14-15) | 27-28 | |
| » Starters: Dennis Bennett vs Larry Jackson | Seventh | 6½ out |
| Former Cub Dick Culler dies in Chapel Hill, NC at the age of 50. |
| Wednesday, June 17 |
| » Defeated Phillies (33-22), 9-5 | Wrigley Field (15-15) | 28-28 | |
| » Starters: Jim Bunning vs Bob Buhl | Fourth | 5½ out |
| Thursday, June 18 |
| » Lost to Phillies (34-22), 6-3 | Wrigley Field (15-16) | 28-29 | |
| » Starters: Chris Short vs Dick Ellsworth | Seventh | 6½ out |
| Saturday, June 20 |
| » Lost to Pirates (33-27), 2-0 | Forbes Field (1-2) | 28-30 | Lost 2 |
| » Starters: Ernie Broglio vs Joe Gibbon | Sixth | 7½ out |
| Sunday, June 21 |
| » Defeated Pirates (33-28), 2-1 | Forbes Field (2-2) | 29-30 | |
| » Starters: Larry Jackson vs Bob Veale | Fifth | 7½ out |
| » Defeated Pirates (33-29), 7-2 | Forbes Field (3-2) | 30-30 | Won 2 |
| » Starters: Lew Burdette vs Steve Blass | Fifth | 7½ out |
| Tuesday, June 23 |
| » Defeated Phillies (38-24), 2-0 | Shibe Park (2-2) | 31-30 | Won 3 |
| » Starters: Dick Ellsworth vs Chris Short | Fifth | 7½ out |
| » Lost to Phillies (39-24), 9-0 | Shibe Park (2-3) | 31-31 | |
| » Starters: Sterling Slaughter vs Ray Culp | Fifth | 7½ out |
| Wednesday, June 24 |
| » Lost to Phillies (40-24), 9-8 | Shibe Park (2-4) | 31-32 | Lost 2 |
| » Starters: Ernie Broglio vs Art Mahaffey | Sixth | 8½ out |
| Friday, June 26 |
| » Defeated Astros (33-37), 7-6 | Wrigley Field (16-16) | 32-32 | |
| » Starters: Ken Johnson vs Larry Jackson | Fifth | 8½ out |
| Saturday, June 27 |
| » Defeated Astros (33-38), 2-1 | Wrigley Field (17-16) | 33-32 | Won 2 |
| » Starters: Turk Farrell vs Dick Ellsworth | Fifth | 7½ out |
| Sunday, June 28 |
| » Defeated Astros (33-39), 10-2 | Wrigley Field (18-16) | 34-32 | Won 3 |
| » Starters: Hal Brown vs Bob Buhl | Fifth | 8 out |
| » Lost to Astros (34-39), 4-1 | Wrigley Field (18-17) | 34-33 | |
| » Starters: Don Nottebart vs Ernie Broglio | Fifth | 8 out |
| » Major-league debuts: Vic Roznovsky (Cubs) |
| Future Cub Mark Grace is born in Winston-Salem, NC. |
| Monday, June 29 |
| » Lost to Reds (38-33), 6-1 | Wrigley Field (18-18) | 34-34 | Lost 2 |
| » Starters: Jim O'Toole vs Lew Burdette | Fifth | 8 out |
| Tuesday, June 30 |
| » Defeated Reds (38-34), 1-0 | Wrigley Field (19-18) | 35-34 | |
| » Starters: Joey Jay vs Larry Jackson | Fifth | 8 out |
| Future Cub Doug Dascenzo is born in Cleveland, OH. |
| Wednesday, July 1 |
| » Lost to Reds (39-34), 6-5 | Crosley Field (2-3) | 35-35 | |
| » Starters: Dick Ellsworth vs Bob Purkey | Fifth | 9 out |
| Thursday, July 2 |
| » Lost to Reds (40-34), 7-0 | Crosley Field (2-4) | 35-36 | Lost 2 |
| » Starters: Ernie Broglio vs Jim Maloney | Sixth | 10 out |
| Friday, July 3 |
| » Lost to Braves (37-39), 8-2 | County Stadium (2-2) | 35-37 | Lost 3 |
| » Starters: Bob Buhl vs Tony Cloninger | Seventh | 10 out |
| Saturday, July 4 |
| » Defeated Braves (37-40), 4-3 | County Stadium (3-2) | 36-37 | |
| » Starters: Larry Jackson vs Denny Lemaster | Fifth | 9½ out |
| Sunday, July 5 |
| » Lost to Braves (38-40), 7-1 | County Stadium (3-3) | 36-38 | |
| » Starters: Dick Ellsworth vs Wade Blasingame | Eighth | 10½ out |
| Wednesday, July 8 |
| » Defeated Giants (47-32), 2-0 | Wrigley Field (20-18) | 37-38 | |
| » Starters: Bob Hendley vs Bob Buhl | Seventh | 10½ out |
| » Lost to Giants (48-32), 7-2 | Wrigley Field (20-19) | 37-39 | |
| » Starters: Ron Herbel vs Ernie Broglio | Seventh | 10½ out |
| Future Cub Ken Patterson is born in Costa Mesa, CA. |
| Thursday, July 9 |
| » Lost to Giants (49-32), 9-4 | Wrigley Field (20-20) | 37-40 | Lost 2 |
| » Starters: Jack Sanford vs Larry Jackson | Eighth | 11½ out |
| Friday, July 10 |
| » Lost to Giants (50-32), 10-3 | Wrigley Field (20-21) | 37-41 | Lost 3 |
| » Starters: Juan Marichal vs Dick Ellsworth | Eighth | 11½ out |
| Saturday, July 11 |
| » Lost to Giants (51-32), 7-0 | Wrigley Field (20-22) | 37-42 | Lost 4 |
| » Starters: Bobby Bolin vs Sterling Slaughter | Eighth | 11½ out |
| Sunday, July 12 |
| » Defeated Dodgers (40-41), 6-3 | Wrigley Field (21-22) | 38-42 | |
| » Starters: Joe Moeller vs Bob Buhl | Seventh | 11½ out |
| » Lost to Dodgers (41-41), 6-2 | Wrigley Field (21-23) | 38-43 | |
| » Starters: Phil Ortega vs Ernie Broglio | Seventh | 11½ out |
| Monday, July 13 |
| » Defeated Dodgers (41-42), 10-4 | Wrigley Field (22-23) | 39-43 | |
| » Starters: Don Drysdale vs Larry Jackson | Eighth | 11½ out |
| Tuesday, July 14 |
| » Defeated Mets (26-61), 4-2 | Wrigley Field (23-23) | 40-43 | Won 2 |
| » Starters: Al Jackson vs Dick Ellsworth | Eighth | 10½ out |
| Wednesday, July 15 |
| » Defeated Mets (26-62), 3-2 | Wrigley Field (24-23) | 41-43 | Won 3 |
| » Starters: Jack Fisher vs Lew Burdette | Seventh | 9½ out |
| Thursday, July 16 |
| » Defeated Mets (26-63), 11-1 | Wrigley Field (25-23) | 42-43 | Won 4 |
| » Starters: Tracy Stallard vs Ernie Broglio | Eighth | 8½ out |
| Friday, July 17 |
| » Lost to Dodgers (44-43), 3-2 | Dodger Stadium (0-2) | 42-44 | |
| » Starters: Bob Buhl vs Don Drysdale | Eighth | 9½ out |
| Saturday, July 18 |
| » Lost to Dodgers (45-43), 3-1 | Dodger Stadium (0-3) | 42-45 | Lost 2 |
| » Starters: Larry Jackson vs Sandy Koufax | Seventh | 9½ out |
| Sunday, July 19 |
| » Defeated Dodgers (45-44), 8-2 | Dodger Stadium (1-3) | 43-45 | |
| » Starters: Dick Ellsworth vs Phil Ortega | Eighth | 8½ out |
| » Defeated Dodgers (45-45), 9-1 | Dodger Stadium (2-3) | 44-45 | Won 2 |
| » Starters: Lew Burdette vs Larry Miller | Eighth | 8½ out |
| Monday, July 20 |
| » Defeated Giants (54-39), 6-4 | Candlestick Park (2-1) | 45-45 | Won 3 |
| » Starters: Ernie Broglio vs Bobby Bolin | Seventh | 7½ out |
| Tuesday, July 21 |
| » Defeated Giants (54-40), 2-1 | Candlestick Park (3-1) | 46-45 | Won 4 |
| » Starters: Bob Buhl vs Gaylord Perry | Seventh | 7½ out |
| Wednesday, July 22 |
| » Lost to Giants (55-40), 7-3 | Candlestick Park (3-2) | 46-46 | |
| » Starters: Larry Jackson vs Ron Herbel | Seventh | 8½ out |
| Thursday, July 23 |
| » Defeated Giants (55-41), 13-4 | Candlestick Park (4-2) | 47-46 | |
| » Starters: Lew Burdette vs Billy O'Dell | Fifth | 8½ out |
| Friday, July 24 |
| » Lost to Astros (44-54), 1-0 | Colt Stadium (2-2) | 47-47 | |
| » Starters: Dick Ellsworth vs Hal Brown | Sixth | 9½ out |
| Saturday, July 25 |
| » Lost to Astros (45-54), 5-3 | Colt Stadium (2-3) | 47-48 | Lost 2 |
| » Starters: Bob Buhl vs Bob Bruce | Seventh | 9½ out |
| Future Cub Jose Bautista is born in Bani, D.R. |
| Sunday, July 26 |
| » Defeated Astros (45-55), 3-0 | Colt Stadium (3-3) | 48-48 | |
| » Starters: Larry Jackson vs Ken Johnson | Seventh | 8 out |
| Tuesday, July 28 |
| » Lost to Cardinals (51-48), 12-7 | Wrigley Field (25-24) | 48-49 | |
| » Starters: Bob Gibson vs Ernie Broglio | Seventh | 9 out |
| Wednesday, July 29 |
| » Lost to Cardinals (52-48), 9-1 | Wrigley Field (25-25) | 48-50 | Lost 2 |
| » Starters: Curt Simmons vs Lew Burdette | Seventh | 9 out |
| Thursday, July 30 |
| » Lost to Cardinals (53-48), 5-2 | Wrigley Field (25-26) | 48-51 | Lost 3 |
| » Starters: Ray Sadecki vs Dick Ellsworth | Eighth | 10 out |
| Friday, July 31 |
| » Lost to Braves (53-48), 13-3 | Wrigley Field (25-27) | 48-52 | Lost 4 |
| » Starters: Bob Sadowski vs Bob Buhl | Eighth | 11 out |
| Saturday, August 1 |
| » Lost to Braves (54-48), 8-4 | Wrigley Field (25-28) | 48-53 | Lost 5 |
| » Starters: Denny Lemaster vs Larry Jackson | Eighth | 12 out |
| Sunday, August 2 |
| » Defeated Braves (54-49), 5-1 | Wrigley Field (26-28) | 49-53 | |
| » Starters: Hank Fischer vs Ernie Broglio | Eighth | 11 out |
| Tuesday, August 4 |
| » Defeated Cardinals (54-51), 4-0 | Sportsman's Park III (2-2) | 50-53 | Won 2 |
| » Starters: Lew Burdette vs Ray Sadecki | Seventh | 10½ out |
| Wednesday, August 5 |
| » Lost to Cardinals (55-51), 4-2 | Sportsman's Park III (2-3) | 50-54 | |
| » Starters: Bob Buhl vs Gordie Richardson | Seventh | 12 out |
| Thursday, August 6 |
| » Lost to Cardinals (56-51), 5-3 | Sportsman's Park III (2-4) | 50-55 | Lost 2 |
| » Starters: Dick Ellsworth vs Bob Gibson | Eighth | 12 out |
| Friday, August 7 |
| » Defeated Pirates (57-49), 7-3 | Forbes Field (4-2) | 51-55 | |
| » Starters: Larry Jackson vs Vern Law | Eighth | 11½ out |
| » Defeated Pirates (57-50), 4-3 | Forbes Field (5-2) | 52-55 | Won 2 |
| » Starters: Ernie Broglio vs Steve Blass | Eighth | 11½ out |
| Saturday, August 8 |
| » Lost to Pirates (58-50), 5-2 | Forbes Field (5-3) | 52-56 | |
| » Starters: Lew Burdette vs Bob Veale | Eighth | 12½ out |
| Sunday, August 9 |
| » Lost to Pirates (59-50), 2-0 | Forbes Field (5-4) | 52-57 | Lost 2 |
| » Starters: Bob Buhl vs Don Schwall | Eighth | 13½ out |
| Tuesday, August 11 |
| » Lost to Phillies (66-43), 13-5 | Wrigley Field (26-29) | 52-58 | Lost 3 |
| » Starters: Ray Culp vs Dick Ellsworth | Eighth | 14½ out |
| Wednesday, August 12 |
| » Lost to Phillies (67-43), 6-5 | Wrigley Field (26-30) | 52-59 | Lost 4 |
| » Starters: Chris Short vs Larry Jackson | Eighth | 15½ out |
| Thursday, August 13 |
| » Defeated Phillies (67-44), 3-1 | Wrigley Field (27-30) | 53-59 | |
| » Starters: Dennis Bennett vs Ernie Broglio | Eighth | 14½ out |
| Friday, August 14 |
| » Lost to Pirates (61-51), 3-2 | Wrigley Field (27-31) | 53-60 | |
| » Starters: Bob Veale vs Bob Buhl | Eighth | 15½ out |
| » Defeated Pirates (61-52), 4-2 | Wrigley Field (28-31) | 54-60 | |
| » Starters: Vern Law vs Lew Burdette | Eighth | 15½ out |
| Future Cub Tommy Shields is born in Fairfax, VA. |
| Saturday, August 15 |
| » Lost to Pirates (62-52), 5-4 | Wrigley Field (28-32) | 54-61 | |
| » Starters: Don Schwall vs Dick Ellsworth | Eighth | 16½ out |
| Future Cub Jeff Huson is born in Scottsdale, AZ. |
| Sunday, August 16 |
| » Defeated Pirates (62-53), 5-4 | Wrigley Field (29-32) | 55-61 | |
| » Starters: Bob Friend vs Larry Jackson | Eighth | 16 out |
| » Lost to Pirates (63-53), 7-4 | Wrigley Field (29-33) | 55-62 | |
| » Starters: Steve Blass vs Sterling Slaughter | Eighth | 16 out |
| Monday, August 17 |
| » Lost to Phillies (71-45), 8-1 | Shibe Park (2-5) | 55-63 | Lost 2 |
| » Starters: Ernie Broglio vs Chris Short | Eighth | 17 out |
| Tuesday, August 18 |
| » Defeated Phillies (71-46), 4-3 | Shibe Park (3-5) | 56-63 | |
| » Starters: Bob Buhl vs Dennis Bennett | Eighth | 16 out |
| Wednesday, August 19 |
| » Lost to Phillies (72-46), 9-5 | Shibe Park (3-6) | 56-64 | |
| » Starters: Dick Ellsworth vs Jim Bunning | Eighth | 17 out |
| Friday, August 21 |
| » Lost to Mets (40-82), 7-0 | Shea Stadium (3-3) | 56-65 | Lost 2 |
| » Starters: Lew Burdette vs Jack Fisher | Eighth | 19 out |
| Saturday, August 22 |
| » Defeated Mets (40-83), 3-2 | Shea Stadium (4-3) | 57-65 | |
| » Starters: Larry Jackson vs Gary Kroll | Eighth | 18 out |
| Sunday, August 23 |
| » Lost to Mets (41-83), 2-1 | Shea Stadium (4-4) | 57-66 | |
| » Starters: Bob Buhl vs Galen Cisco | Seventh | 19½ out |
| » Lost to Mets (42-83), 5-4 | Shea Stadium (4-5) | 57-67 | Lost 2 |
| » Starters: Dick Ellsworth vs Dennis Ribant | Seventh | 19½ out |
| Monday, August 24 |
| » Lost to Astros (55-71), 2-0 | Colt Stadium (3-4) | 57-68 | Lost 3 |
| » Starters: Lew Burdette vs Bob Bruce | Eighth | 19½ out |
| Tuesday, August 25 |
| » Lost to Astros (56-71), 5-4 | Colt Stadium (3-5) | 57-69 | Lost 4 |
| » Starters: John Flavin vs Ken Johnson | Eighth | 19½ out |
| Wednesday, August 26 |
| » Defeated Astros (56-72), 3-1 | Colt Stadium (4-5) | 58-69 | |
| » Starters: Larry Jackson vs Hal Brown | Eighth | 19½ out |
| Friday, August 28 |
| » Lost to Mets (44-84), 12-10 | Wrigley Field (29-34) | 58-70 | |
| » Starters: Jack Fisher vs Bob Buhl | Eighth | 19½ out |
| Saturday, August 29 |
| » Defeated Mets (44-85), 4-3 | Wrigley Field (30-34) | 59-70 | |
| » Starters: Galen Cisco vs Dick Ellsworth | Eighth | 19½ out |
| Sunday, August 30 |
| » Defeated Mets (44-86), 7-3 | Wrigley Field (31-34) | 60-70 | Won 2 |
| » Starters: Dennis Ribant vs Larry Jackson | Seventh | 18½ out |
| Tuesday, September 1 |
| » Lost to Reds (74-57), 2-1 | Crosley Field (2-5) | 60-71 | |
| » Starters: Ernie Broglio vs Jim Maloney | Eighth | 19½ out |
| Wednesday, September 2 |
| » Lost to Reds (75-57), 1-0 | Crosley Field (2-6) | 60-72 | Lost 2 |
| » Starters: Bob Buhl vs Jim O'Toole | Eighth | 20½ out |
| Thursday, September 3 |
| » Defeated Reds (75-58), 3-0 | Crosley Field (3-6) | 61-72 | |
| » Starters: Lew Burdette vs John Tsitouris | Eighth | 19½ out |
| Friday, September 4 |
| » Lost to Cardinals (74-60), 8-5 | Sportsman's Park III (2-5) | 61-73 | |
| » Starters: Dick Ellsworth vs Curt Simmons | Eighth | 20½ out |
| Saturday, September 5 |
| » Defeated Cardinals (74-61), 8-5 | Sportsman's Park III (3-5) | 62-73 | |
| » Starters: Larry Jackson vs Mike Cuellar | Eighth | 20½ out |
| Sunday, September 6 |
| » Lost to Cardinals (75-61), 5-4 | Sportsman's Park III (3-6) | 62-74 | |
| » Starters: Ernie Broglio vs Ray Sadecki | Eighth | 20½ out |
| Monday, September 7 |
| » Lost to Braves (69-68), 10-9 | Wrigley Field (31-35) | 62-75 | Lost 2 |
| » Starters: Dan Schneider vs Lew Burdette | Seventh | 21½ out |
| » Lost to Braves (70-68), 8-7 | Wrigley Field (31-36) | 62-76 | Lost 3 |
| » Starters: Clay Carroll vs Bob Buhl | Seventh | 21½ out |
| » Major-league debuts: Don Kessinger (Cubs) |
| Wednesday, September 9 |
| » Defeated Astros (58-83), 6-3 | Wrigley Field (32-36) | 63-76 | |
| » Starters: Bob Bruce vs Dick Ellsworth | Eighth | 20 out |
| Thursday, September 10 |
| » Defeated Astros (58-84), 4-3 | Wrigley Field (33-36) | 64-76 | Won 2 |
| » Starters: Ken Johnson vs Larry Jackson | Seventh | 20 out |
| Friday, September 11 |
| » Lost to Cardinals (79-62), 5-0 | Wrigley Field (33-37) | 64-77 | |
| » Starters: Bob Gibson vs Ernie Broglio | Eighth | 21 out |
| Saturday, September 12 |
| » Defeated Cardinals (79-63), 3-2 | Wrigley Field (34-37) | 65-77 | |
| » Starters: Roger Craig vs Bob Buhl | Eighth | 20 out |
| Sunday, September 13 |
| » Lost to Cardinals (80-63), 15-2 | Wrigley Field (34-38) | 65-78 | |
| » Starters: Curt Simmons vs Dick Ellsworth | Eighth | 21 out |
| Tuesday, September 15 |
| » Defeated Reds (79-65), 6-1 | Wrigley Field (35-38) | 66-78 | |
| » Starters: Bob Purkey vs Larry Jackson | Eighth | 21½ out |
| Wednesday, September 16 |
| » Lost to Reds (80-65), 5-3 | Wrigley Field (35-39) | 66-79 | |
| » Starters: Jim Maloney vs Bob Buhl | Eighth | 21½ out |
| Thursday, September 17 |
| » Lost to Reds (81-65), 7-5 | Wrigley Field (35-40) | 66-80 | Lost 2 |
| » Starters: Jim O'Toole vs Lew Burdette | Eighth | 22½ out |
| Saturday, September 19 |
| » Defeated Braves (75-72), 5-3 | County Stadium (4-3) | 67-80 | |
| » Starters: Larry Jackson vs Hank Fischer | Eighth | 21½ out |
| » Lost to Braves (76-72), 8-5 | County Stadium (4-4) | 67-81 | |
| » Starters: Dick Ellsworth vs Tony Cloninger | Eighth | 21½ out |
| Sunday, September 20 |
| » Lost to Braves (77-72), 5-2 | County Stadium (4-5) | 67-82 | Lost 2 |
| » Starters: Bob Buhl vs Wade Blasingame | Seventh | 22½ out |
| Tuesday, September 22 |
| » Defeated Dodgers (75-76), 1-0 | Wrigley Field (36-40) | 68-82 | |
| » Starters: Don Drysdale vs Lew Burdette | Eighth | 21 out |
| Wednesday, September 23 |
| » Defeated Dodgers (75-77), 9-6 | Wrigley Field (37-40) | 69-82 | Won 2 |
| » Starters: Pete Richert vs Larry Jackson | Eighth | 20 out |
| Thursday, September 24 |
| » Defeated Dodgers (75-78), 4-3 | Wrigley Field (38-40) | 70-82 | Won 3 |
| » Starters: Bill Singer vs Dick Ellsworth | Eighth | 19 out |
| Future Cub Rafael Palmeiro is born in Havana, Cuba. |
| Friday, September 25 |
| » Lost to Giants (86-68), 3-1 | Wrigley Field (38-41) | 70-83 | |
| » Starters: Gaylord Perry vs Bob Buhl | Eighth | 19 out |
| Saturday, September 26 |
| Future Cub Dave Martinez is born in New York, NY. |
| Sunday, September 27 |
| » Defeated Giants (86-69), 4-1 | Wrigley Field (39-41) | 71-83 | |
| » Starters: Juan Marichal vs Larry Jackson | Eighth | 18 out |
| » Defeated Giants (86-70), 4-2 | Wrigley Field (40-41) | 72-83 | Won 2 |
| » Starters: Bobby Bolin vs Cal Koonce | Eighth | 18 out |
| » Major-league debuts: Randy Hundley (Giants) |
| Monday, September 28 |
| » Lost to Dodgers (77-79), 2-1 | Dodger Stadium (2-4) | 72-84 | |
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