| Saturday, January 5 |
| Former Cub Rogers Hornsby dies in Chicago, IL at the age of 67. |
| Saturday, January 26 |
| Future Cub Kevin Blankenship is born in Anaheim, CA. |
| Saturday, February 9 |
| Former Cub Ray Starr dies in Baylis, IL at the age of 57. |
| Saturday, March 9 |
| Future Cub Terry Mulholland is born in Uniontown, PA. |
| Thursday, March 21 |
| Future Cub Shawon Dunston is born in Brooklyn, NY. |
| Wednesday, March 27 |
| Future Cub Drew Hall is born in Louisville, KY. |
| Monday, April 8 |
| » Major-league debuts: Tom Brown (Senators) |
| Tuesday, April 9 |
| » Lost to Dodgers (1-0), 5-1 | Wrigley Field (0-1) | 0-1 | |
| » Starters: Don Drysdale vs Larry Jackson | Third | 1 out |
| » Major-league debuts: Nate Oliver (Dodgers) |
| Future Cub Mike Brumley is born in Oklahoma City, OK. Future Cub Jose Guzman is born in Santa Isabel, P.R. |
| Wednesday, April 10 |
| » Lost to Dodgers (2-0), 2-1 | Wrigley Field (0-2) | 0-2 | Lost 2 |
| » Starters: Sandy Koufax vs Bob Buhl | Fourth | 2 out |
| Thursday, April 11 |
| » Defeated Dodgers (2-1), 2-0 | Wrigley Field (1-2) | 1-2 | |
| » Starters: Johnny Podres vs Dick Ellsworth | Fourth | 2 out |
| Saturday, April 13 |
| » Lost to Giants (4-0), 2-1 | Wrigley Field (1-3) | 1-3 | |
| » Starters: Jack Sanford vs Glen Hobbie | Seventh | 3 out |
| Sunday, April 14 |
| » Defeated Giants (4-1), 3-1 | Wrigley Field (2-3) | 2-3 | |
| » Starters: Juan Marichal vs Larry Jackson | Fourth | 2 out |
| » Major-league debuts: Jose Cardenal (Giants) |
| Tuesday, April 16 |
| » Defeated Dodgers (3-4), 2-1 | Dodger Stadium (1-0) | 3-3 | Won 2 |
| » Starters: Bob Buhl vs Johnny Podres | Fourth | 2 out |
| Wednesday, April 17 |
| » Lost to Dodgers (4-4), 1-0 | Dodger Stadium (1-1) | 3-4 | |
| » Starters: Dick Ellsworth vs Bob Miller | Fifth | 2½ out |
| Thursday, April 18 |
| » Defeated Dodgers (4-5), 5-1 | Dodger Stadium (2-1) | 4-4 | |
| » Starters: Glen Hobbie vs Don Drysdale | Fourth | 2½ out |
| Friday, April 19 |
| » Lost to Giants (7-2), 5-1 | Candlestick Park (0-1) | 4-5 | |
| » Starters: Larry Jackson vs Juan Marichal | Sixth | 3 out |
| Saturday, April 20 |
| » Defeated Giants (7-3), 4-0 | Candlestick Park (1-1) | 5-5 | |
| » Starters: Bob Buhl vs Billy Pierce | Fifth | 2 out |
| Sunday, April 21 |
| » Defeated Giants (7-4), 4-1 | Candlestick Park (2-1) | 6-5 | Won 2 |
| » Starters: Dick Ellsworth vs Jack Fisher | Fifth | 2 out |
| » Lost to Giants (8-4), 3-2 | Candlestick Park (2-2) | 6-6 | |
| » Starters: Cal Koonce vs Billy O'Dell | Fifth | 2 out |
| Monday, April 22 |
| » Lost to Pirates (7-4), 2-0 | Forbes Field (0-1) | 6-7 | Lost 2 |
| » Starters: Glen Hobbie vs Earl Francis | Seventh | 2 out |
| Tuesday, April 23 |
| » Defeated Pirates (7-5), 7-2 | Forbes Field (1-1) | 7-7 | |
| » Starters: Larry Jackson vs Don Cardwell | Fifth | 2 out |
| Wednesday, April 24 |
| » Lost to Mets (5-9), 2-0 | Wrigley Field (2-4) | 7-8 | |
| » Starters: Carl Willey vs Bob Buhl | Sixth | 3 out |
| Thursday, April 25 |
| » Lost to Mets (6-9), 3-2 | Wrigley Field (2-5) | 7-9 | Lost 2 |
| » Starters: Roger Craig vs Dick Ellsworth | Sixth | 3 out |
| Friday, April 26 |
| » Lost to Phillies (8-7), 5-2 | Wrigley Field (2-6) | 7-10 | Lost 3 |
| » Starters: Art Mahaffey vs Glen Hobbie | Sixth | 4 out |
| Saturday, April 27 |
| » Defeated Phillies (8-8), 4-2 | Wrigley Field (3-6) | 8-10 | |
| » Starters: Ray Culp vs Larry Jackson | Seventh | 4 out |
| Sunday, April 28 |
| » Defeated Phillies (8-9), 4-1 | Wrigley Field (4-6) | 9-10 | Won 2 |
| » Starters: Chris Short vs Bob Buhl | Sixth | 3½ out |
| Wednesday, May 1 |
| » Defeated Cardinals (14-7), 13-8 | Sportsman's Park III (1-0) | 10-10 | Won 3 |
| » Starters: Dick Ellsworth vs Ray Sadecki | Fifth | 3½ out |
| Thursday, May 2 |
| » Lost to Cardinals (15-7), 4-3 | Sportsman's Park III (1-1) | 10-11 | |
| » Starters: Larry Jackson vs Ray Washburn | Sixth | 4½ out |
| Friday, May 3 |
| » Defeated Braves (13-11), 10-7 | County Stadium (1-0) | 11-11 | |
| » Starters: Bob Buhl vs Warren Spahn | Fifth | 3½ out |
| Future Cub Joe Kmak is born in Napa, CA. |
| Saturday, May 4 |
| » Defeated Braves (13-12), 7-5 | County Stadium (2-0) | 12-11 | Won 2 |
| » Starters: Glen Hobbie vs Bob Shaw | Third | 2½ out |
| Sunday, May 5 |
| » Defeated Braves (13-13), 3-2 | County Stadium (3-0) | 13-11 | Won 3 |
| » Starters: Cal Koonce vs Tony Cloninger | Third | 1½ out |
| Tuesday, May 7 |
| » Defeated Pirates (14-9), 5-4 | Wrigley Field (5-6) | 14-11 | Won 4 |
| » Starters: Don Cardwell vs Larry Jackson | Fourth | 2 out |
| Wednesday, May 8 |
| » Defeated Pirates (14-10), 9-5 | Wrigley Field (6-6) | 15-11 | Won 5 |
| » Starters: Al McBean vs Bob Buhl | Third | 2 out |
| Thursday, May 9 |
| » Defeated Pirates (14-11), 3-1 | Wrigley Field (7-6) | 16-11 | Won 6 |
| » Starters: Don Schwall vs Dick Ellsworth | Second | 2 out |
| Friday, May 10 |
| » Lost to Astros (10-19), 4-1 | Colt Stadium (0-1) | 16-12 | |
| » Starters: Glen Hobbie vs Turk Farrell | Third | 2 out |
| Saturday, May 11 |
| » Lost to Astros (11-19), 5-3 | Colt Stadium (0-2) | 16-13 | Lost 2 |
| » Starters: Cal Koonce vs Hal Brown | Fourth | 2½ out |
| » Lost to Astros (12-19), 1-0 | Colt Stadium (0-3) | 16-14 | Lost 3 |
| » Starters: Larry Jackson vs Dick Drott | Fourth | 2½ out |
| Sunday, May 12 |
| » Lost to Astros (13-19), 2-1 | Colt Stadium (0-4) | 16-15 | Lost 4 |
| » Starters: Bob Buhl vs Don Nottebart | Fifth | 2½ out |
| Tuesday, May 14 |
| » Defeated Reds (14-16), 2-1 | Wrigley Field (8-6) | 17-15 | |
| » Starters: Joe Nuxhall vs Dick Ellsworth | Fourth | 2½ out |
| Wednesday, May 15 |
| » Lost to Reds (15-16), 10-2 | Wrigley Field (8-7) | 17-16 | |
| » Starters: Jim Maloney vs Glen Hobbie | Fifth | 3½ out |
| Thursday, May 16 |
| » Defeated Reds (15-17), 2-0 | Wrigley Field (9-7) | 18-16 | |
| » Starters: Jim O'Toole vs Larry Jackson | Third | 3½ out |
| Saturday, May 18 |
| » Lost to Braves (18-19), 10-6 | Wrigley Field (9-8) | 18-17 | |
| » Starters: Bob Shaw vs Bob Buhl | Fourth | 4 out |
| Sunday, May 19 |
| » Defeated Braves (18-20), 3-2 | Wrigley Field (10-8) | 19-17 | |
| » Starters: Lew Burdette vs Dick Ellsworth | Third | 4 out |
| » Lost to Braves (19-20), 8-2 | Wrigley Field (10-9) | 19-18 | |
| » Starters: Warren Spahn vs Cal Koonce | Third | 4 out |
| Tuesday, May 21 |
| » Lost to Cardinals (21-19), 5-4 | Wrigley Field (10-10) | 19-19 | Lost 2 |
| » Starters: Curt Simmons vs Larry Jackson | Fifth | 5 out |
| Wednesday, May 22 |
| » Defeated Cardinals (21-20), 7-6 | Wrigley Field (11-10) | 20-19 | |
| » Starters: Ray Washburn vs Bob Buhl | Third | 5 out |
| Former Cub Dave Shean dies in Boston, MA at the age of 80. |
| Thursday, May 23 |
| » Lost to Cardinals (22-20), 1-0 | Wrigley Field (11-11) | 20-20 | |
| » Starters: Ernie Broglio vs Dick Ellsworth | Sixth | 5½ out |
| Friday, May 24 |
| » Lost to Astros (19-24), 6-5 | Wrigley Field (11-12) | 20-21 | Lost 2 |
| » Starters: Bob Bruce vs Cal Koonce | Sixth | 6½ out |
| Saturday, May 25 |
| » Defeated Astros (19-25), 4-1 | Wrigley Field (12-12) | 21-21 | |
| » Starters: Turk Farrell vs Larry Jackson | Sixth | 6½ out |
| Sunday, May 26 |
| » Defeated Astros (19-26), 5-1 | Wrigley Field (13-12) | 22-21 | Won 2 |
| » Starters: Dick Drott vs Bob Buhl | Fourth | 5½ out |
| Tuesday, May 28 |
| » Defeated Mets (17-29), 5-2 | Polo Grounds V (1-0) | 23-21 | Won 3 |
| » Starters: Dick Ellsworth vs Roger Craig | Fourth | 4½ out |
| Thursday, May 30 |
| » Defeated Mets (17-30), 12-0 | Polo Grounds V (2-0) | 24-21 | Won 4 |
| » Starters: Larry Jackson vs Al Jackson | Fourth | 5½ out |
| » Lost to Mets (18-30), 2-1 | Polo Grounds V (2-1) | 24-22 | |
| » Starters: Glen Hobbie vs Jay Hook | Fourth | 5½ out |
| Friday, May 31 |
| » Defeated Phillies (22-25), 2-1 | Shibe Park (1-0) | 25-22 | |
| » Starters: Bob Buhl vs Chris Short | Fourth | 4½ out |
| Saturday, June 1 |
| » Defeated Phillies (22-26), 2-0 | Shibe Park (2-0) | 26-22 | Won 2 |
| » Starters: Dick Ellsworth vs John Boozer | Fourth | 3½ out |
| Sunday, June 2 |
| » Lost to Phillies (23-26), 5-2 | Shibe Park (2-1) | 26-23 | |
| » Starters: Jim Brewer vs Cal McLish | Fourth | 4 out |
| » Defeated Phillies (23-27), 3-2 | Shibe Park (3-1) | 27-23 | |
| » Starters: Cal Koonce vs Art Mahaffey | Fourth | 4 out |
| Tuesday, June 4 |
| » Defeated Giants (31-20), 6-1 | Wrigley Field (14-12) | 28-23 | Won 2 |
| » Starters: Billy O'Dell vs Bob Buhl | Third | 3 out |
| Wednesday, June 5 |
| » Defeated Giants (31-21), 9-5 | Wrigley Field (15-12) | 29-23 | Won 3 |
| » Starters: Jack Fisher vs Dick Ellsworth | Second | 1 out |
| » Defeated Giants (31-22), 5-4 | Wrigley Field (16-12) | 30-23 | Won 4 |
| » Starters: Jack Sanford vs Glen Hobbie | Second | 1 out |
| Thursday, June 6 |
| » Defeated Giants (31-23), 3-2 | Wrigley Field (17-12) | 31-23 | Won 5 |
| » Starters: Juan Marichal vs Larry Jackson | First | -- |
| Friday, June 7 |
| » Lost to Dodgers (30-23), 4-1 | Wrigley Field (17-13) | 31-24 | |
| » Starters: Don Drysdale vs Paul Toth | Second | 1 out |
| Saturday, June 8 |
| » Lost to Dodgers (31-23), 9-5 | Wrigley Field (17-14) | 31-25 | Lost 2 |
| » Starters: Johnny Podres vs Bob Buhl | Third | 1 out |
| Sunday, June 9 |
| » Lost to Dodgers (32-23), 11-8 | Wrigley Field (17-15) | 31-26 | Lost 3 |
| » Starters: Sandy Koufax vs Dick Ellsworth | Third | 2 out |
| Monday, June 10 |
| » Defeated Astros (25-33), 3-2 | Colt Stadium (1-4) | 32-26 | |
| » Starters: Glen Hobbie vs Dick Drott | Third | 1 out |
| Tuesday, June 11 |
| » Lost to Astros (26-33), 6-2 | Colt Stadium (1-5) | 32-27 | |
| » Starters: Larry Jackson vs Ken Johnson | Fourth | 2 out |
| Wednesday, June 12 |
| » Lost to Giants (34-26), 3-1 | Candlestick Park (2-3) | 32-28 | Lost 2 |
| » Starters: Bob Buhl vs Bobby Bolin | Third | 2 out |
| Thursday, June 13 |
| » Lost to Giants (35-26), 2-1 | Candlestick Park (2-4) | 32-29 | Lost 3 |
| » Starters: Dick Ellsworth vs Billy O'Dell | Fourth | 3 out |
| Friday, June 14 |
| » Defeated Dodgers (34-26), 4-1 | Dodger Stadium (3-1) | 33-29 | |
| » Starters: Glen Hobbie vs Bob Miller | Third | 3 out |
| Saturday, June 15 |
| » Lost to Dodgers (35-26), 4-1 | Dodger Stadium (3-2) | 33-30 | |
| » Starters: Larry Jackson vs Don Drysdale | Fourth | 4 out |
| Sunday, June 16 |
| » Defeated Dodgers (35-27), 8-3 | Dodger Stadium (4-2) | 34-30 | |
| » Starters: Bob Buhl vs Johnny Podres | Fifth | 4 out |
| » Lost to Dodgers (36-27), 2-0 | Dodger Stadium (4-3) | 34-31 | |
| » Starters: Paul Toth vs Nick Willhite | Fifth | 4 out |
| » Major-league debuts: Nick Willhite (Dodgers) |
| Tuesday, June 18 |
| » Defeated Astros (27-39), 3-1 | Wrigley Field (18-15) | 35-31 | |
| » Starters: Bob Bruce vs Dick Ellsworth | Fifth | 4 out |
| Wednesday, June 19 |
| » Defeated Astros (27-40), 9-1 | Wrigley Field (19-15) | 36-31 | Won 2 |
| » Starters: Hal Brown vs Glen Hobbie | Fifth | 4 out |
| Thursday, June 20 |
| » Defeated Astros (27-41), 5-0 | Wrigley Field (20-15) | 37-31 | Won 3 |
| » Starters: Dick Drott vs Larry Jackson | Fifth | 3½ out |
| Friday, June 21 |
| » Defeated Pirates (31-36), 6-5 | Wrigley Field (21-15) | 38-31 | Won 4 |
| » Starters: Don Cardwell vs Bob Buhl | Fifth | 2½ out |
| Saturday, June 22 |
| » Lost to Pirates (32-36), 3-0 | Wrigley Field (21-16) | 38-32 | |
| » Starters: Bob Friend vs Dick Ellsworth | Fourth | 3½ out |
| Sunday, June 23 |
| » Lost to Pirates (33-36), 7-6 | Wrigley Field (21-17) | 38-33 | Lost 2 |
| » Starters: Vern Law vs Glen Hobbie | Fifth | 3½ out |
| Tuesday, June 25 |
| » Defeated Mets (28-45), 4-1 | Polo Grounds V (3-1) | 39-33 | |
| » Starters: Larry Jackson vs Jay Hook | Fifth | 3 out |
| Wednesday, June 26 |
| » Lost to Mets (29-45), 8-6 | Polo Grounds V (3-2) | 39-34 | |
| » Starters: Bob Buhl vs Al Jackson | Fifth | 4 out |
| Friday, June 28 |
| » Defeated Phillies (34-41), 4-3 | Shibe Park (4-1) | 40-34 | |
| » Starters: Dick Ellsworth vs Ryne Duren | Fourth | 4 out |
| Sunday, June 30 |
| » Lost to Phillies (35-41), 3-2 | Shibe Park (4-2) | 40-35 | |
| » Starters: Larry Jackson vs Art Mahaffey | Fifth | 4½ out |
| Tuesday, July 2 |
| » Defeated Mets (29-49), 4-1 | Wrigley Field (22-17) | 41-35 | |
| » Starters: Al Jackson vs Bob Buhl | Fifth | 3½ out |
| Wednesday, July 3 |
| » Defeated Mets (29-50), 9-2 | Wrigley Field (23-17) | 42-35 | Won 2 |
| » Starters: Jay Hook vs Dick Ellsworth | Fifth | 3½ out |
| Thursday, July 4 |
| » Defeated Mets (29-51), 2-1 | Wrigley Field (24-17) | 43-35 | Won 3 |
| » Starters: Roger Craig vs Glen Hobbie | Third | 3 out |
| » Defeated Mets (29-52), 3-0 | Wrigley Field (25-17) | 44-35 | Won 4 |
| » Starters: Carl Willey vs Paul Toth | Third | 3 out |
| Friday, July 5 |
| » Defeated Phillies (38-44), 3-2 | Wrigley Field (26-17) | 45-35 | Won 5 |
| » Starters: Ray Culp vs Larry Jackson | Second | 3 out |
| Saturday, July 6 |
| » Lost to Phillies (39-44), 6-0 | Wrigley Field (26-18) | 45-36 | |
| » Starters: Cal McLish vs Bob Buhl | Third | 3 out |
| Future Cub Lance Johnson is born in Cincinnati, OH. |
| Sunday, July 7 |
| » Lost to Phillies (40-44), 3-2 | Wrigley Field (26-19) | 45-37 | Lost 2 |
| » Starters: Art Mahaffey vs Dick Ellsworth | Third | 4½ out |
| Wednesday, July 10 |
| » Lost to Reds (46-40), 3-1 | Crosley Field (0-1) | 45-38 | Lost 3 |
| » Starters: Glen Hobbie vs Joey Jay | Fourth | 5½ out |
| Thursday, July 11 |
| » Defeated Reds (46-41), 7-0 | Crosley Field (1-1) | 46-38 | |
| » Starters: Dick Ellsworth vs Joe Nuxhall | Fourth | 6 out |
| » Lost to Reds (47-41), 7-3 | Crosley Field (1-2) | 46-39 | |
| » Starters: Paul Toth vs Jim Maloney | Fourth | 6 out |
| Friday, July 12 |
| » Defeated Reds (47-42), 4-1 | Crosley Field (2-2) | 47-39 | |
| » Starters: Bob Buhl vs Jim O'Toole | Fourth | 6 out |
| Sunday, July 14 |
| » Lost to Cardinals (49-40), 10-3 | Sportsman's Park III (1-2) | 47-40 | |
| » Starters: Glen Hobbie vs Ray Sadecki | Third | 7 out |
| » Defeated Cardinals (49-41), 7-3 | Sportsman's Park III (2-2) | 48-40 | |
| » Starters: Larry Jackson vs Ron Taylor | Third | 7 out |
| Monday, July 15 |
| » Defeated Cardinals (49-42), 2-0 | Sportsman's Park III (3-2) | 49-40 | Won 2 |
| » Starters: Dick Ellsworth vs Ernie Broglio | Second | 6 out |
| Tuesday, July 16 |
| » Defeated Braves (46-45), 1-0 | Wrigley Field (27-19) | 50-40 | Won 3 |
| » Starters: Bob Sadowski vs Bob Buhl | Second | 5½ out |
| Wednesday, July 17 |
| » Lost to Braves (47-45), 6-4 | Wrigley Field (27-20) | 50-41 | |
| » Starters: Hank Fischer vs Glen Hobbie | Second | 6½ out |
| Thursday, July 18 |
| » Defeated Braves (47-46), 3-2 | Wrigley Field (28-20) | 51-41 | |
| » Starters: Tony Cloninger vs Larry Jackson | Second | 6½ out |
| Friday, July 19 |
| » Lost to Pirates (48-46), 9-4 | Forbes Field (1-2) | 51-42 | |
| » Starters: Dick Ellsworth vs Bob Friend | Second | 7½ out |
| Sunday, July 21 |
| » Defeated Pirates (48-47), 5-1 | Forbes Field (2-2) | 52-42 | |
| » Starters: Paul Toth vs Don Cardwell | Third | 7 out |
| » Lost to Pirates (49-47), 6-5 | Forbes Field (2-3) | 52-43 | |
| » Starters: Dick LeMay vs Don Schwall | Third | 7 out |
| Tuesday, July 23 |
| » Lost to Reds (53-46), 1-0 | Wrigley Field (28-21) | 52-44 | Lost 2 |
| » Starters: Jim Maloney vs Larry Jackson | Third | 8 out |
| Wednesday, July 24 |
| » Defeated Reds (53-47), 2-1 | Wrigley Field (29-21) | 53-44 | |
| » Starters: Bob Purkey vs Dick Ellsworth | Third | 8 out |
| Thursday, July 25 |
| » Lost to Reds (54-47), 3-2 | Wrigley Field (29-22) | 53-45 | |
| » Starters: John Tsitouris vs Bob Buhl | Fourth | 8 out |
| Friday, July 26 |
| » Lost to Cardinals (57-44), 4-1 | Wrigley Field (29-23) | 53-46 | Lost 2 |
| » Starters: Bob Gibson vs Paul Toth | Fifth | 8 out |
| Saturday, July 27 |
| » Lost to Cardinals (58-44), 3-2 | Wrigley Field (29-24) | 53-47 | Lost 3 |
| » Starters: Curt Simmons vs Larry Jackson | Fifth | 8 out |
| Sunday, July 28 |
| » Defeated Cardinals (58-45), 5-1 | Wrigley Field (30-24) | 54-47 | |
| » Starters: Ray Sadecki vs Dick Ellsworth | Third | 6½ out |
| » Defeated Cardinals (58-46), 16-11 | Wrigley Field (31-24) | 55-47 | Won 2 |
| » Starters: Ernie Broglio vs Glen Hobbie | Third | 6½ out |
| Tuesday, July 30 |
| » Lost to Braves (54-52), 9-2 | County Stadium (3-1) | 55-48 | |
| » Starters: Bob Buhl vs Hank Fischer | Fourth | 7 out |
| Wednesday, July 31 |
| » Defeated Braves (54-53), 3-2 | County Stadium (4-1) | 56-48 | |
| » Starters: Paul Toth vs Tony Cloninger | Fourth | 7 out |
| Thursday, August 1 |
| » Defeated Braves (54-54), 10-2 | County Stadium (5-1) | 57-48 | Won 2 |
| » Starters: Larry Jackson vs Denny Lemaster | Third | 6½ out |
| Friday, August 2 |
| » Defeated Giants (60-48), 12-11 | Wrigley Field (32-24) | 58-48 | Won 3 |
| » Starters: Jack Sanford vs Dick Ellsworth | Fourth | 5½ out |
| » Major-league debuts: Tom Baker (Cubs) |
| Former Cub Pete Standridge dies in San Francisco, CA at the age of 73. |
| Saturday, August 3 |
| » Lost to Giants (61-48), 9-5 | Wrigley Field (32-25) | 58-49 | |
| » Starters: Jack Sanford vs Bob Buhl | Fourth | 6½ out |
| Sunday, August 4 |
| » Lost to Giants (62-48), 2-1 | Wrigley Field (32-26) | 58-50 | Lost 2 |
| » Starters: Billy O'Dell vs Paul Toth | Fourth | 7½ out |
| Former Cub Bob Fisher dies in Jacksonville, FL at the age of 77. |
| Tuesday, August 6 |
| » Lost to Dodgers (67-43), 4-1 | Wrigley Field (32-27) | 58-51 | Lost 3 |
| » Starters: Don Drysdale vs Larry Jackson | Third | 8½ out |
| Wednesday, August 7 |
| » Lost to Dodgers (68-43), 3-1 | Wrigley Field (32-28) | 58-52 | Lost 4 |
| » Starters: Sandy Koufax vs Dick Ellsworth | Third | 9½ out |
| Thursday, August 8 |
| » Defeated Dodgers (68-44), 5-4 | Wrigley Field (33-28) | 59-52 | |
| » Starters: Bob Miller vs Bob Buhl | Fourth | 8½ out |
| Friday, August 9 |
| » Lost to Mets (37-77), 7-3 | Polo Grounds V (3-3) | 59-53 | |
| » Starters: Paul Toth vs Roger Craig | Fifth | 8½ out |
| Saturday, August 10 |
| » Defeated Mets (37-78), 4-0 | Polo Grounds V (4-3) | 60-53 | |
| » Starters: Larry Jackson vs Galen Cisco | Fourth | 8½ out |
| Sunday, August 11 |
| » Defeated Mets (37-79), 8-1 | Polo Grounds V (5-3) | 61-53 | Won 2 |
| » Starters: Dick Ellsworth vs Carl Willey | Fifth | 8 out |
| » Lost to Mets (38-79), 11-4 | Polo Grounds V (5-4) | 61-54 | |
| » Starters: Bob Buhl vs Tracy Stallard | Fifth | 8 out |
| Wednesday, August 14 |
| » Lost to Phillies (62-58), 7-2 | Shibe Park (4-3) | 61-55 | Lost 2 |
| » Starters: Larry Jackson vs Ray Culp | Sixth | 8 out |
| » Lost to Phillies (63-58), 9-3 | Shibe Park (4-4) | 61-56 | Lost 3 |
| » Starters: Paul Toth vs Dennis Bennett | Sixth | 8 out |
| Thursday, August 15 |
| » Lost to Phillies (64-58), 4-3 | Shibe Park (4-5) | 61-57 | Lost 4 |
| » Starters: Bob Buhl vs Cal McLish | Sixth | 9 out |
| Friday, August 16 |
| » Defeated Reds (65-59), 10-1 | Crosley Field (3-2) | 62-57 | |
| » Starters: Dick Ellsworth vs Jim O'Toole | Sixth | 9½ out |
| » Lost to Reds (66-59), 8-2 | Crosley Field (3-3) | 62-58 | |
| » Starters: Glen Hobbie vs Joey Jay | Sixth | 9½ out |
| Saturday, August 17 |
| » Lost to Reds (67-59), 2-1 | Crosley Field (3-4) | 62-59 | Lost 2 |
| » Starters: Tom Baker vs Bob Purkey | Sixth | 10½ out |
| Sunday, August 18 |
| » Defeated Reds (67-60), 2-1 | Crosley Field (4-4) | 63-59 | |
| » Starters: Larry Jackson vs Jim Maloney | Fifth | 10½ out |
| » Defeated Reds (67-61), 4-0 | Crosley Field (5-4) | 64-59 | Won 2 |
| » Starters: Paul Toth vs John Tsitouris | Fifth | 10½ out |
| Tuesday, August 20 |
| » Lost to Pirates (62-61), 5-3 | Wrigley Field (33-29) | 64-60 | |
| » Starters: Don Cardwell vs Bob Buhl | Seventh | 11½ out |
| Future Cub Kal Daniels is born in Vienna, GA. |
| Wednesday, August 21 |
| » Lost to Pirates (63-61), 7-6 | Wrigley Field (33-30) | 64-61 | Lost 2 |
| » Starters: Joe Gibbon vs Dick Ellsworth | Seventh | 12½ out |
| Thursday, August 22 |
| » Lost to Pirates (64-61), 9-3 | Wrigley Field (33-31) | 64-62 | Lost 3 |
| » Starters: Bob Friend vs Larry Jackson | Eighth | 12½ out |
| Friday, August 23 |
| » Defeated Mets (40-87), 6-5 | Wrigley Field (34-31) | 65-62 | |
| » Starters: Tracy Stallard vs Paul Toth | Seventh | 11½ out |
| Saturday, August 24 |
| » Lost to Mets (41-87), 5-0 | Wrigley Field (34-32) | 65-63 | |
| » Starters: Carl Willey vs Cal Koonce | Seventh | 11½ out |
| Sunday, August 25 |
| » Defeated Mets (41-88), 3-1 | Wrigley Field (35-32) | 66-63 | |
| » Starters: Jay Hook vs Dick Ellsworth | Sixth | 11½ out |
| Monday, August 26 |
| » Major-league debuts: Dwight Siebler (Twins) |
| Tuesday, August 27 |
| » Defeated Phillies (71-61), 4-3 | Wrigley Field (36-32) | 67-63 | Won 2 |
| » Starters: Dennis Bennett vs Larry Jackson | Sixth | 11 out |
| Wednesday, August 28 |
| » Lost to Phillies (72-61), 8-7 | Wrigley Field (36-33) | 67-64 | |
| » Starters: Chris Short vs Paul Toth | Eighth | 11 out |
| Thursday, August 29 |
| » Defeated Phillies (72-62), 2-1 | Wrigley Field (37-33) | 68-64 | |
| » Starters: John Boozer vs Dick Ellsworth | Seventh | 11 out |
| Friday, August 30 |
| » Lost to Astros (50-84), 5-1 | Wrigley Field (37-34) | 68-65 | |
| » Starters: Ken Johnson vs Cal Koonce | Seventh | 12 out |
| Saturday, August 31 |
| » Defeated Astros (50-85), 6-5 | Wrigley Field (38-34) | 69-65 | |
| » Starters: Hal Brown vs Larry Jackson | Seventh | 11 out |
| Sunday, September 1 |
| » Defeated Astros (50-86), 4-3 | Wrigley Field (39-34) | 70-65 | Won 2 |
| » Starters: Don Nottebart vs Bob Buhl | Seventh | 11 out |
| Monday, September 2 |
| » Defeated Giants (74-63), 7-5 | Candlestick Park (3-4) | 71-65 | Won 3 |
| » Starters: Dick Ellsworth vs Bobby Bolin | Sixth | 11 out |
| » Defeated Giants (74-64), 6-0 | Candlestick Park (4-4) | 72-65 | Won 4 |
| » Starters: Glen Hobbie vs Jack Fisher | Sixth | 11 out |
| » Major-league debuts: John Boccabella (Cubs) |
| Tuesday, September 3 |
| » Lost to Giants (75-64), 16-3 | Candlestick Park (4-5) | 72-66 | |
| » Starters: Larry Jackson vs Juan Marichal | Seventh | 12 out |
| » Major-league debuts: Jimmy Stewart (Cubs) |
| Future Cub Ced Landrum is born in Butler, AL. |
| Wednesday, September 4 |
| » Defeated Dodgers (84-55), 2-1 | Dodger Stadium (5-3) | 73-66 | |
| » Starters: Cal Koonce vs Bob Miller | Sixth | 11 out |
| Thursday, September 5 |
| » Lost to Dodgers (85-55), 4-0 | Dodger Stadium (5-4) | 73-67 | |
| » Starters: Bob Buhl vs Pete Richert | Sixth | 12 out |
| Friday, September 6 |
| » Defeated Astros (51-91), 3-0 | Colt Stadium (2-5) | 74-67 | |
| » Starters: Glen Hobbie vs Hal Brown | Sixth | 12 out |
| Saturday, September 7 |
| » Lost to Astros (52-91), 2-1 | Colt Stadium (2-6) | 74-68 | |
| » Starters: Dick Ellsworth vs Turk Farrell | Seventh | 12 out |
| Sunday, September 8 |
| » Lost to Astros (53-91), 2-1 | Colt Stadium (2-7) | 74-69 | Lost 2 |
| » Starters: Larry Jackson vs Ken Johnson | Seventh | 12 out |
| Monday, September 9 |
| » Lost to Cardinals (84-61), 6-0 | Sportsman's Park III (3-3) | 74-70 | Lost 3 |
| » Starters: Cal Koonce vs Curt Simmons | Seventh | 12½ out |
| » Major-league debuts: Billy Cowan (Cubs) |
| Tuesday, September 10 |
| » Lost to Cardinals (85-61), 8-0 | Sportsman's Park III (3-4) | 74-71 | Lost 4 |
| » Starters: Glen Hobbie vs Bob Gibson | Seventh | 13½ out |
| Wednesday, September 11 |
| » Lost to Cardinals (86-61), 4-0 | Sportsman's Park III (3-5) | 74-72 | Lost 5 |
| » Starters: Dick Ellsworth vs Ray Sadecki | Seventh | 14½ out |
| Thursday, September 12 |
| » Lost to Cardinals (87-61), 8-3 | Sportsman's Park III (3-6) | 74-73 | Lost 6 |
| » Starters: Larry Jackson vs Ernie Broglio | Seventh | 15½ out |
| Friday, September 13 |
| » Defeated Reds (78-73), 3-2 | Wrigley Field (40-34) | 75-73 | |
| » Starters: Joe Nuxhall vs Paul Toth | Seventh | 15 out |
| Saturday, September 14 |
| » Lost to Reds (79-73), 8-4 | Wrigley Field (40-35) | 75-74 | |
| » Starters: Dom Zanni vs Cal Koonce | Sixth | 16 out |
| Sunday, September 15 |
| » Lost to Reds (80-73), 3-1 | Wrigley Field (40-36) | 75-75 | Lost 2 |
| » Starters: John Tsitouris vs Dick Ellsworth | Seventh | 16 out |
| Monday, September 16 |
| » Lost to Pirates (71-79), 1-0 | Forbes Field (2-4) | 75-76 | Lost 3 |
| » Starters: Larry Jackson vs Bob Veale | Seventh | 17 out |
| Tuesday, September 17 |
| » Defeated Pirates (71-80), 3-1 | Forbes Field (3-4) | 76-76 | |
| » Starters: Bob Buhl vs Bob Friend | Seventh | 17½ out |
| » Lost to Pirates (72-80), 4-3 | Forbes Field (3-5) | 76-77 | |
| » Starters: Glen Hobbie vs Tommie Sisk | Seventh | 17½ out |
| Wednesday, September 18 |
| » Defeated Pirates (72-81), 2-1 | Forbes Field (4-5) | 77-77 | |
| » Starters: Cal Koonce vs Joe Gibbon | Seventh | 17½ out |
| Friday, September 20 |
| » Defeated Braves (81-74), 1-0 | Wrigley Field (41-36) | 78-77 | Won 2 |
| » Starters: Denny Lemaster vs Dick Ellsworth | Seventh | 17½ out |
| Saturday, September 21 |
| » Lost to Braves (82-74), 4-0 | Wrigley Field (41-37) | 78-78 | |
| » Starters: Warren Spahn vs Larry Jackson | Sixth |
