| Sunday, January 11 |
| Future Cub Lloyd McClendon is born in Gary, IN. |
| Wednesday, January 14 |
| Former Cub John Ganzel dies in Orlando, FL at the age of 85. |
| Wednesday, February 4 |
| Future Cub Pat Perry is born in Taylorville, IL. |
| Thursday, February 12 |
| Former Cub Dode Paskert dies in Cleveland, OH at the age of 78. |
| Thursday, April 2 |
| Future Cub Al Nipper is born in San Diego, CA. |
| Saturday, April 11 |
| » Defeated Dodgers (0-1), 6-1 | Wrigley Field (1-0) | 1-0 | |
| » Starters: Don Drysdale vs Bob Anderson | Second | ½ out |
| » Major-league debuts: George Altman (Cubs) Jim Baxes (Dodgers) |
| Sunday, April 12 |
| » Lost to Dodgers (1-1), 5-3 | Wrigley Field (1-1) | 1-1 | |
| » Starters: Sandy Koufax vs Taylor Phillips | Fourth | 1½ out |
| » Major-league debuts: Norm Sherry (Dodgers) |
| Tuesday, April 14 |
| » Defeated Giants (3-1), 5-2 | Seals Stadium (1-0) | 2-1 | |
| » Starters: Dave Hillman vs Jack Sanford | Third | 1 out |
| Wednesday, April 15 |
| » Lost to Giants (4-1), 7-1 | Seals Stadium (1-1) | 2-2 | |
| » Starters: Moe Drabowsky vs Johnny Antonelli | Fifth | 1½ out |
| » Major-league debuts: Joe Schaffernoth (Cubs) |
| Thursday, April 16 |
| » Defeated Giants (4-2), 11-3 | Seals Stadium (2-1) | 3-2 | |
| » Starters: Glen Hobbie vs Sam Jones | Fourth | 1½ out |
| Friday, April 17 |
| » Defeated Dodgers (3-3), 9-4 | Los Angeles Memorial Coliseum (1-0) | 4-2 | Won 2 |
| » Starters: Dick Drott vs Stan Williams | Second | 1 out |
| Saturday, April 18 |
| » Lost to Dodgers (4-3), 8-7 | Los Angeles Memorial Coliseum (1-1) | 4-3 | |
| » Starters: Joe Schaffernoth vs Danny McDevitt | Fourth | 1 out |
| Future Cub Rich Bordi is born in San Francisco, CA. Future Cub Dennis Rasmussen is born in Los Angeles, CA. |
| Sunday, April 19 |
| » Lost to Dodgers (5-3), 8-3 | Los Angeles Memorial Coliseum (1-2) | 4-4 | Lost 2 |
| » Starters: Dave Hillman vs Johnny Podres | Sixth | 1½ out |
| Tuesday, April 21 |
| » Defeated Cardinals (2-8), 1-0 | Wrigley Field (2-1) | 5-4 | |
| » Starters: Gary Blaylock vs Glen Hobbie | Third | 1½ out |
| Wednesday, April 22 |
| » Lost to Cardinals (3-8), 8-2 | Wrigley Field (2-2) | 5-5 | |
| » Starters: Vinegar Bend Mizell vs Taylor Phillips | Fourth | 2½ out |
| Future Cub Terry Francona is born in Aberdeen, SD. |
| Thursday, April 23 |
| » Defeated Cardinals (3-9), 6-1 | Wrigley Field (3-2) | 6-5 | |
| » Starters: Lindy McDaniel vs Moe Drabowsky | Fourth | 1½ out |
| Friday, April 24 |
| » Lost to Giants (8-5), 4-3 | Wrigley Field (3-3) | 6-6 | |
| » Starters: Johnny Antonelli vs Dave Hillman | Fourth | 2½ out |
| » Major-league debuts: Don Eaddy (Cubs) |
| Saturday, April 25 |
| » Defeated Giants (8-6), 5-3 | Wrigley Field (4-3) | 7-6 | |
| » Starters: Sam Jones vs Bob Anderson | Fourth | 1½ out |
| Sunday, April 26 |
| » Lost to Giants (9-6), 3-2 | Wrigley Field (4-4) | 7-7 | |
| » Starters: Jack Sanford vs Glen Hobbie | Fifth | 2 out |
| Wednesday, April 29 |
| » Lost to Reds (8-6), 18-8 | Crosley Field (0-1) | 7-8 | Lost 2 |
| » Starters: Moe Drabowsky vs Brooks Lawrence | Fifth | 2½ out |
| Thursday, April 30 |
| » Defeated Reds (8-7), 3-2 | Crosley Field (1-1) | 8-8 | |
| » Starters: Bob Anderson vs Bob Purkey | Fifth | 2½ out |
| Friday, May 1 |
| » Lost to Phillies (7-8), 4-2 | Shibe Park (0-1) | 8-9 | |
| » Starters: Glen Hobbie vs Jim Owens | Fifth | 2½ out |
| Saturday, May 2 |
| » Defeated Phillies (7-9), 4-3 | Shibe Park (1-1) | 9-9 | |
| » Starters: Dave Hillman vs Seth Morehead | Fifth | 2 out |
| Sunday, May 3 |
| » Defeated Phillies (7-10), 4-3 | Shibe Park (2-1) | 10-9 | Won 2 |
| » Starters: Dick Drott vs Chris Short | Fourth | 2 out |
| » Lost to Phillies (8-10), 5-4 | Shibe Park (2-2) | 10-10 | |
| » Starters: Moe Drabowsky vs Ruben Gomez | Fourth | 2 out |
| Monday, May 4 |
| » Lost to Pirates (9-10), 2-1 | Forbes Field (0-1) | 10-11 | Lost 2 |
| » Starters: Bob Anderson vs Ron Kline | Fifth | 2½ out |
| Tuesday, May 5 |
| » Defeated Pirates (9-11), 6-3 | Forbes Field (1-1) | 11-11 | |
| » Starters: Glen Hobbie vs Bob Friend | Fourth | 2 out |
| Wednesday, May 6 |
| » Defeated Pirates (9-12), 3-0 | Forbes Field (2-1) | 12-11 | Won 2 |
| » Starters: Dave Hillman vs Harvey Haddix | Fourth | 2 out |
| Thursday, May 7 |
| » Lost to Cardinals (8-16), 4-3 | Sportsman's Park III (0-1) | 12-12 | |
| » Starters: Moe Drabowsky vs Lindy McDaniel | Fifth | 2½ out |
| Friday, May 8 |
| » Defeated Cardinals (8-17), 3-2 | Sportsman's Park III (1-1) | 13-12 | |
| » Starters: Bob Anderson vs Gary Blaylock | Fifth | 2½ out |
| Saturday, May 9 |
| » Lost to Cardinals (9-17), 11-1 | Sportsman's Park III (1-2) | 13-13 | |
| » Starters: Glen Hobbie vs Larry Jackson | Fifth | 2½ out |
| Sunday, May 10 |
| » Defeated Cardinals (9-18), 10-9 | Sportsman's Park III (2-2) | 14-13 | |
| » Starters: Dave Hillman vs Vinegar Bend Mizell | Fifth | 2½ out |
| » Lost to Cardinals (10-18), 8-7 | Sportsman's Park III (2-3) | 14-14 | |
| » Starters: John Buzhardt vs Ernie Broglio | Fifth | 2½ out |
| Monday, May 11 |
| » Lost to Braves (15-9), 8-1 | Wrigley Field (4-5) | 14-15 | Lost 2 |
| » Starters: Bob Buhl vs Moe Drabowsky | Fifth | 3½ out |
| Tuesday, May 12 |
| » Defeated Braves (15-10), 7-3 | Wrigley Field (5-5) | 15-15 | |
| » Starters: Lew Burdette vs Bob Anderson | Fifth | 3 out |
| Wednesday, May 13 |
| » Defeated Reds (14-13), 10-0 | Wrigley Field (6-5) | 16-15 | Won 2 |
| » Starters: Bob Purkey vs Glen Hobbie | Fifth | 2½ out |
| Thursday, May 14 |
| » Lost to Reds (15-13), 2-0 | Wrigley Field (6-6) | 16-16 | |
| » Starters: Joe Nuxhall vs Dave Hillman | Sixth | 3½ out |
| Saturday, May 16 |
| » Defeated Pirates (15-16), 3-2 | Wrigley Field (7-6) | 17-16 | |
| » Starters: Harvey Haddix vs Moe Drabowsky | Fifth | 3½ out |
| Future Cub Bob Patterson is born in Jacksonville, FL. Future Cub Mitch Webster is born in Larned, KS. |
| Sunday, May 17 |
| » Lost to Pirates (16-16), 5-4 | Wrigley Field (7-7) | 17-17 | |
| » Starters: Vern Law vs Bob Anderson | Fifth | 4 out |
| » Defeated Pirates (16-17), 7-6 | Wrigley Field (8-7) | 18-17 | |
| » Starters: Bennie Daniels vs Glen Hobbie | Fifth | 4 out |
| Monday, May 18 |
| Former Cub Gene Packard dies in Riverside, CA at the age of 72. |
| Tuesday, May 19 |
| » Defeated Phillies (11-21), 8-7 | Wrigley Field (9-7) | 19-17 | Won 2 |
| » Starters: Gene Conley vs Dave Hillman | Third | 4½ out |
| Wednesday, May 20 |
| » Defeated Phillies (11-22), 7-5 | Wrigley Field (10-7) | 20-17 | Won 3 |
| » Starters: Don Cardwell vs Moe Drabowsky | Third | 3½ out |
| Thursday, May 21 |
| » Lost to Phillies (12-22), 3-0 | Wrigley Field (10-8) | 20-18 | |
| » Starters: Ruben Gomez vs Bob Anderson | Third | 4 out |
| Friday, May 22 |
| » Lost to Cardinals (16-21), 3-1 | Wrigley Field (10-9) | 20-19 | Lost 2 |
| » Starters: Gary Blaylock vs Glen Hobbie | Fourth | 5 out |
| Saturday, May 23 |
| » Lost to Cardinals (17-21), 5-1 | Wrigley Field (10-10) | 20-20 | Lost 3 |
| » Starters: Larry Jackson vs Dave Hillman | Fifth | 5 out |
| Sunday, May 24 |
| » Lost to Cardinals (18-21), 7-3 | Wrigley Field (10-11) | 20-21 | Lost 4 |
| » Starters: Vinegar Bend Mizell vs Moe Drabowsky | Fifth | 5½ out |
| Monday, May 25 |
| » Defeated Cardinals (18-22), 9-4 | Sportsman's Park III (3-3) | 21-21 | |
| » Starters: Bob Anderson vs Tom Cheney | Fifth | 4½ out |
| Wednesday, May 27 |
| » Lost to Dodgers (23-21), 4-1 | Los Angeles Memorial Coliseum (1-3) | 21-22 | |
| » Starters: Glen Hobbie vs Don Drysdale | Sixth | 6 out |
| Thursday, May 28 |
| » Defeated Dodgers (23-22), 7-5 | Los Angeles Memorial Coliseum (2-3) | 22-22 | |
| » Starters: Seth Morehead vs Stan Williams | Fifth | 5 out |
| Former Cub Ken Penner dies in Sacramento, CA at the age of 64. |
| Friday, May 29 |
| » Defeated Dodgers (23-23), 9-4 | Los Angeles Memorial Coliseum (3-3) | 23-22 | Won 2 |
| » Starters: Moe Drabowsky vs Danny McDevitt | Third | 5 out |
| Saturday, May 30 |
| » Lost to Giants (25-19), 5-2 | Seals Stadium (2-2) | 23-23 | |
| » Starters: Bob Anderson vs Mike McCormick | Fifth | 6 out |
| Sunday, May 31 |
| » Lost to Giants (26-19), 6-3 | Seals Stadium (2-3) | 23-24 | Lost 2 |
| » Starters: Glen Hobbie vs Johnny Antonelli | Fifth | 6½ out |
| Wednesday, June 3 |
| » Lost to Phillies (18-29), 4-3 | Shibe Park (2-3) | 23-25 | Lost 3 |
| » Starters: Dave Hillman vs Jim Owens | Fifth | 7½ out |
| Thursday, June 4 |
| » Defeated Phillies (18-30), 3-2 | Shibe Park (3-3) | 24-25 | |
| » Starters: Bob Anderson vs Gene Conley | Fifth | 6½ out |
| Friday, June 5 |
| » Defeated Pirates (28-23), 10-5 | Forbes Field (3-1) | 25-25 | Won 2 |
| » Starters: Glen Hobbie vs Vern Law | Fifth | 5½ out |
| Saturday, June 6 |
| » Defeated Pirates (28-24), 8-2 | Forbes Field (4-1) | 26-25 | Won 3 |
| » Starters: Moe Drabowsky vs Bennie Daniels | Fifth | 4½ out |
| Sunday, June 7 |
| » Defeated Pirates (28-25), 4-2 | Forbes Field (5-1) | 27-25 | Won 4 |
| » Starters: John Buzhardt vs Harvey Haddix | Third | 4 out |
| » Defeated Pirates (28-26), 1-0 | Forbes Field (6-1) | 28-25 | Won 5 |
| » Starters: Elmer Singleton vs Bob Friend | Third | 4 out |
| Monday, June 8 |
| » Lost to Braves (32-20), 9-5 | County Stadium (0-1) | 28-26 | |
| » Starters: Seth Morehead vs Lew Burdette | Fourth | 5 out |
| Tuesday, June 9 |
| » Defeated Reds (25-29), 8-4 | Wrigley Field (11-11) | 29-26 | |
| » Starters: Joe Nuxhall vs Bob Anderson | Third | 4 out |
| Wednesday, June 10 |
| » Lost to Reds (26-29), 6-4 | Wrigley Field (11-12) | 29-27 | |
| » Starters: Bob Purkey vs Glen Hobbie | Third | 4 out |
| Thursday, June 11 |
| » Lost to Reds (27-29), 8-0 | Wrigley Field (11-13) | 29-28 | Lost 2 |
| » Starters: Don Newcombe vs Moe Drabowsky | Fifth | 5 out |
| Friday, June 12 |
| » Defeated Braves (33-23), 9-7 | Wrigley Field (12-13) | 30-28 | |
| » Starters: Lew Burdette vs John Buzhardt | Fourth | 4 out |
| Saturday, June 13 |
| » Lost to Braves (34-23), 4-2 | Wrigley Field (12-14) | 30-29 | |
| » Starters: Warren Spahn vs Bob Anderson | Fifth | 5 out |
| Sunday, June 14 |
| » Defeated Braves (34-24), 6-0 | Wrigley Field (13-14) | 31-29 | |
| » Starters: Bob Rush vs Dick Drott | Fourth | 4 out |
| Tuesday, June 16 |
| » Lost to Pirates (34-29), 5-2 | Wrigley Field (13-15) | 31-30 | |
| » Starters: Bob Friend vs Dave Hillman | Fifth | 4½ out |
| Wednesday, June 17 |
| » Defeated Pirates (34-30), 5-2 | Wrigley Field (14-15) | 32-30 | |
| » Starters: Harvey Haddix vs John Buzhardt | Fifth | 3 out |
| Thursday, June 18 |
| » Lost to Pirates (35-30), 4-2 | Wrigley Field (14-16) | 32-31 | |
| » Starters: Ron Kline vs Moe Drabowsky | Fifth | 4 out |
| Friday, June 19 |
| » Lost to Phillies (24-38), 8-7 | Wrigley Field (14-17) | 32-32 | Lost 2 |
| » Starters: Gene Conley vs Bob Anderson | Fifth | 4½ out |
| Saturday, June 20 |
| » Lost to Phillies (25-38), 6-3 | Wrigley Field (14-18) | 32-33 | Lost 3 |
| » Starters: Robin Roberts vs Dick Drott | Fifth | 5 out |
| Sunday, June 21 |
| » Defeated Phillies (25-39), 4-0 | Wrigley Field (15-18) | 33-33 | |
| » Starters: Ruben Gomez vs John Buzhardt | Fifth | 5 out |
| Tuesday, June 23 |
| » Defeated Reds (30-37), 3-1 | Crosley Field (2-1) | 34-33 | Won 2 |
| » Starters: Glen Hobbie vs Joe Nuxhall | Fourth | 5 out |
| Wednesday, June 24 |
| » Lost to Reds (31-37), 5-0 | Crosley Field (2-2) | 34-34 | |
| » Starters: Dick Drott vs Jim Brosnan | Fifth | 6 out |
| Thursday, June 25 |
| » Defeated Reds (31-38), 6-2 | Crosley Field (3-2) | 35-34 | |
| » Starters: Bob Anderson vs Bob Purkey | Fifth | 5 out |
| Friday, June 26 |
| » Lost to Braves (41-29), 11-1 | County Stadium (0-2) | 35-35 | |
| » Starters: John Buzhardt vs Warren Spahn | Fifth | 6 out |
| Saturday, June 27 |
| » Defeated Braves (41-30), 7-1 | County Stadium (1-2) | 36-35 | |
| » Starters: Glen Hobbie vs Carl Willey | Fifth | 5 out |
| Sunday, June 28 |
| » Lost to Braves (42-30), 2-1 | County Stadium (1-3) | 36-36 | |
| » Starters: Dave Hillman vs Juan Pizarro | Fifth | 6 out |
| Tuesday, June 30 |
| » Lost to Cardinals (35-38), 4-1 | Wrigley Field (15-19) | 36-37 | Lost 2 |
| » Starters: Larry Jackson vs Bob Anderson | Fifth | 6 out |
| Wednesday, July 1 |
| » Defeated Cardinals (35-39), 6-5 | Wrigley Field (16-19) | 37-37 | |
| » Starters: Ernie Broglio vs John Buzhardt | Fifth | 5½ out |
| Thursday, July 2 |
| » Defeated Giants (43-34), 10-4 | Wrigley Field (17-19) | 38-37 | Won 2 |
| » Starters: Eddie Fisher vs Glen Hobbie | Fifth | 4½ out |
| Friday, July 3 |
| » Lost to Giants (44-34), 4-0 | Wrigley Field (17-20) | 38-38 | |
| » Starters: Johnny Antonelli vs Dave Hillman | Fifth | 5½ out |
| Saturday, July 4 |
| » Defeated Dodgers (44-37), 2-1 | Wrigley Field (18-20) | 39-38 | |
| » Starters: Larry Sherry vs Bob Anderson | Fifth | 5½ out |
| » Lost to Dodgers (45-37), 5-2 | Wrigley Field (18-21) | 39-39 | |
| » Starters: Don Drysdale vs Moe Drabowsky | Fifth | 5½ out |
| Sunday, July 5 |
| » Lost to Dodgers (46-37), 4-3 | Wrigley Field (18-22) | 39-40 | Lost 2 |
| » Starters: Roger Craig vs John Buzhardt | Fifth | 6½ out |
| » Lost to Dodgers (47-37), 5-3 | Wrigley Field (18-23) | 39-41 | Lost 3 |
| » Starters: Stan Williams vs Dick Drott | Fifth | 6½ out |
| Thursday, July 9 |
| » Lost to Pirates (45-39), 4-3 | Forbes Field (6-2) | 39-42 | Lost 4 |
| » Starters: Bob Anderson vs Vern Law | Fifth | 7½ out |
| Friday, July 10 |
| » Lost to Pirates (46-39), 7-6 | Forbes Field (6-3) | 39-43 | Lost 5 |
| » Starters: Glen Hobbie vs Bob Friend | Fifth | 8½ out |
| Saturday, July 11 |
| » Defeated Pirates (46-40), 5-1 | Forbes Field (7-3) | 40-43 | |
| » Starters: Dave Hillman vs Ron Kline | Fifth | 8½ out |
| Sunday, July 12 |
| » Defeated Phillies (30-53), 7-6 | Shibe Park (4-3) | 41-43 | Won 2 |
| » Starters: Art Ceccarelli vs Ruben Gomez | Fifth | 8 out |
| » Lost to Phillies (31-53), 4-1 | Shibe Park (4-4) | 41-44 | |
| » Starters: Moe Drabowsky vs Ray Semproch | Fifth | 8 out |
| Monday, July 13 |
| Former Cub Chick Keating dies in Philadelphia, PA at the age of 68. |
| Tuesday, July 14 |
| » Defeated Braves (46-36), 10-5 | Wrigley Field (19-23) | 42-44 | |
| » Starters: Juan Pizarro vs Bob Anderson | Fifth | 7 out |
| Wednesday, July 15 |
| » Defeated Braves (46-37), 5-2 | Wrigley Field (20-23) | 43-44 | Won 2 |
| » Starters: Carl Willey vs Glen Hobbie | Fifth | 6½ out |
| Thursday, July 16 |
| » Defeated Braves (46-38), 4-2 | Wrigley Field (21-23) | 44-44 | Won 3 |
| » Starters: Lew Burdette vs Dave Hillman | Fifth | 6 out |
| Friday, July 17 |
| » Defeated Reds (39-50), 1-0 | Wrigley Field (22-23) | 45-44 | Won 4 |
| » Starters: Bob Purkey vs Art Ceccarelli | Fifth | 6 out |
| Saturday, July 18 |
| » Lost to Reds (40-50), 5-1 | Wrigley Field (22-24) | 45-45 | |
| » Starters: Jay Hook vs John Buzhardt | Fifth | 7 out |
| Monday, July 20 |
| » Lost to Cardinals (46-46), 2-0 | Sportsman's Park III (3-4) | 45-46 | Lost 2 |
| » Starters: Glen Hobbie vs Ernie Broglio | Sixth | 6½ out |
| Tuesday, July 21 |
| » Defeated Cardinals (46-47), 8-2 | Sportsman's Park III (4-4) | 46-46 | |
| » Starters: Art Ceccarelli vs Larry Jackson | Fifth | 5½ out |
| Wednesday, July 22 |
| » Defeated Dodgers (53-44), 7-2 | Los Angeles Memorial Coliseum (4-3) | 47-46 | Won 2 |
| » Starters: Bob Anderson vs Danny McDevitt | Fifth | 5½ out |
| Thursday, July 23 |
| » Lost to Dodgers (54-44), 5-3 | Los Angeles Memorial Coliseum (4-4) | 47-47 | |
| » Starters: Moe Drabowsky vs Larry Sherry | Fifth | 6½ out |
| Friday, July 24 |
| » Lost to Giants (55-41), 6-5 | Seals Stadium (2-4) | 47-48 | Lost 2 |
| » Starters: Dave Hillman vs Johnny Antonelli | Fifth | 7½ out |
| Saturday, July 25 |
| » Defeated Giants (55-42), 5-3 | Seals Stadium (3-4) | 48-48 | |
| » Starters: Art Ceccarelli vs Stu Miller | Fifth | 6½ out |
| Sunday, July 26 |
| » Defeated Giants (55-43), 7-3 | Seals Stadium (4-4) | 49-48 | Won 2 |
| » Starters: Bob Anderson vs Mike McCormick | Fourth | 5½ out |
| Tuesday, July 28 |
| » Defeated Braves (52-44), 5-4 | County Stadium (2-3) | 50-48 | Won 3 |
| » Starters: Glen Hobbie vs Juan Pizarro | Fourth | 4½ out |
| Wednesday, July 29 |
| » Lost to Braves (53-44), 8-5 | County Stadium (2-4) | 50-49 | |
| » Starters: Dave Hillman vs Lew Burdette | Fourth | 5 out |
| Thursday, July 30 |
| » Lost to Braves (54-44), 6-2 | County Stadium (2-5) | 50-50 | Lost 2 |
| » Starters: Art Ceccarelli vs Warren Spahn | Fourth | 5½ out |
| Friday, July 31 |
| » Lost to Reds (47-55), 5-4 | Crosley Field (3-3) | 50-51 | Lost 3 |
| » Starters: Bob Anderson vs Don Newcombe | Fourth | 6½ out |
| Future Cub Mike Bielecki is born in Baltimore, MD. |
| Saturday, August 1 |
| » Lost to Reds (48-55), 12-3 | Crosley Field (3-4) | 50-52 | Lost 4 |
| » Starters: Glen Hobbie vs Bob Purkey | Fourth | 7½ out |
| Sunday, August 2 |
| » Lost to Reds (49-55), 2-0 | Crosley Field (3-5) | 50-53 | Lost 5 |
| » Starters: Dave Hillman vs Jay Hook | Fourth | 8½ out |
| Tuesday, August 4 |
| » Lost to Phillies (43-60), 2-1 | Wrigley Field (22-25) | 50-54 | Lost 6 |
| » Starters: Robin Roberts vs Bob Anderson | Fourth | 8½ out |
| Former Cub Pop Williams dies in Topsham, ME at the age of 86. |
| Wednesday, August 5 |
| » Lost to Phillies (44-60), 6-4 | Wrigley Field (22-26) | 50-55 | Lost 7 |
| » Starters: Gene Conley vs Glen Hobbie | Fourth | 9½ out |
| Thursday, August 6 |
| » Defeated Phillies (44-61), 4-2 | Wrigley Field (23-26) | 51-55 | |
| » Starters: Jim Owens vs Art Ceccarelli | Fourth | 9½ out |
| » Major-league debuts: Billy Williams (Cubs) |
| Friday, August 7 |
| » Defeated Pirates (52-58), 4-0 | Wrigley Field (24-26) | 52-55 | Won 2 |
| » Starters: Ron Kline vs Moe Drabowsky | Fourth | 9½ out |
| Saturday, August 8 |
| » Lost to Pirates (53-58), 4-3 | Wrigley Field (24-27) | 52-56 | |
| » Starters: George Witt vs Bob Anderson | Fifth | 9½ out |
| Future Cub Dave Meier is born in Helena, MT. |
| Sunday, August 9 |
| » Lost to Pirates (54-58), 5-3 | Wrigley Field (24-28) | 52-57 | Lost 2 |
| » Starters: Vern Law vs Dave Hillman | Fifth | 10½ out |
| Tuesday, August 11 |
| » Defeated Dodgers (62-50), 5-4 | Wrigley Field (25-28) | 53-57 | |
| » Starters: Johnny Podres vs Moe Drabowsky | Fourth | 11 out |
| Wednesday, August 12 |
| » Defeated Dodgers (62-51), 11-8 | Wrigley Field (26-28) | 54-57 | Won 2 |
| » Starters: Don Drysdale vs Bob Anderson | Fourth | 10½ out |
| Thursday, August 13 |
| » Defeated Giants (65-48), 20-9 | Wrigley Field (27-28) | 55-57 | Won 3 |
| » Starters: Jack Sanford vs Art Ceccarelli | Fourth | 9½ out |
| Friday, August 14 |
| » Defeated Giants (65-49), 7-5 | Wrigley Field (28-28) | 56-57 | Won 4 |
| » Starters: Sam Jones vs Glen Hobbie | Fourth | 8½ out |
| Saturday, August 15 |
| » Lost to Giants (66-49), 6-4 | Wrigley Field (28-29) | 56-58 | |
| » Starters: Jack Sanford vs Moe Drabowsky | Fourth | 9½ out |
| Sunday, August 16 |
| » Defeated Giants (66-50), 5-4 | Wrigley Field (29-29) | 57-58 | |
| » Starters: Johnny Antonelli vs Bob Anderson | Fourth | 8½ out |
| Monday, August 17 |
| » Lost to Pirates (59-60), 7-6 | Forbes Field (7-4) | 57-59 | |
| » Starters: Dave Hillman vs Harvey Haddix | Fifth | 9½ out |
| Wednesday, August 19 |
| » Lost to Phillies (51-69), 4-1 | Shibe Park (4-5) | 57-60 | Lost 2 |
| » Starters: Glen Hobbie vs Gene Conley | Fifth | 9 out |
| » Tied Phillies, 7-7 | Shibe Park (4-5) | 57-60 | |
| » Starters: Art Ceccarelli vs Don Cardwell | Fifth | 9 out |
| Thursday, August 20 |
| » Lost to Phillies (52-69), 8-5 | Shibe Park (4-6) | 57-61 | Lost 3 |
| » Starters: Moe Drabowsky vs Ruben Gomez | Fifth | 9½ out |
| » Defeated Phillies (52-70), 6-4 | Shibe Park (5-6) | 58-61 | |
| » Starters: Bob Anderson vs Taylor Phillips | Fifth | 9½ out |
| Saturday, August 22 |
| » Lost to Braves (65-56), 7-0 | County Stadium (2-6) | 58-62 | |
| » Starters: Glen Hobbie vs Carl Willey | Sixth | 12 out |
| » Lost to Braves (66-56), 3-2 | County Stadium (2-7) | 58-63 | Lost 2 |
| » Starters: Dave Hillman vs Joey Jay | Sixth | 12 out |
| Sunday, August 23 |
| » Lost to Braves (67-56), 2-0 | County Stadium (2-8) | 58-64 | Lost 3 |
| » Starters: Art Ceccarelli vs Bob Buhl | Sixth | 12½ out |
| Monday, August 24 |
| » Defeated Braves (67-57), 3-0 | County Stadium (3-8) | 59-64 | |
| » Starters: Bob Anderson vs Lew Burdette | Sixth | 11½ out |
| Tuesday, August 25 |
| » Defeated Reds (61-65), 8-6 | Crosley Field (4-5) | 60-64 | Won 2 |
| » Starters: John Buzhardt vs Bob Purkey | Fifth | 11½ out |
| Wednesday, August 26 |
| » Defeated Reds (61-66), 9-5 | Crosley Field (5-5) | 61-64 | Won 3 |
| » Starters: Glen Hobbie vs Jay Hook | Fifth | 10½ out |
| Thursday, August 27 |
| » Lost to Reds (62-66), 5-0 | Crosley Field (5-6) | 61-65 | |
| » Starters: Art Ceccarelli vs Jim O'Toole | Fifth | 10 out |
| Former Cub Claude Jonnard dies in Nashville, TN at the age of 62. |
| Friday, August 28 |
| » Lost to Braves (69-59), 9-3 | Wrigley Field (29-30) | 61-66 | Lost 2 |
| » Starters: Lew Burdette vs Bob Anderson | Sixth | 11 out |
| Saturday, August 29 |
| » Lost to Braves (70-59), 11-4 | Wrigley Field (29-31) | 61-67 | Lost 3 |
| » Starters: Warren Spahn vs Moe Drabowsky | Fourth | 11½ out |
| Sunday, August 30 |
| » Defeated Braves (70-60), 6-2 | Wrigley Field (30-31) | 62-67 | |
| » Starters: Carl Willey vs Glen Hobbie | Fifth | 10½ out |
| Wednesday, September 2 |
| » Lost to Giants (74-58), 4-3 | Seals Stadium (4-5) | 62-68 | |
| » Starters: Art Ceccarelli vs Mike McCormick | Sixth | 11 out |
| Thursday, September 3 |
| » Lost to Giants (75-58), 8-5 | Seals Stadium (4-6) | 62-69 | Lost 2 |
| » Starters: Bob Anderson vs Johnny Antonelli | Sixth | 12 out |
| Friday, September 4 |
| » Defeated Giants (75-59), 2-1 | Seals Stadium (5-6) | 63-69 | |
| » Starters: Glen Hobbie vs Jack Sanford | Sixth | 11 out |
| Sunday, September 6 |
| » Defeated Dodgers (73-62), 3-0 | Los Angeles Memorial Coliseum (5-4) | 64-69 | Won 2 |
| » Starters: Art Ceccarelli vs Sandy Koufax | Fifth | 10 out |
| » Defeated Dodgers (73-63), 5-3 | Los Angeles Memorial Coliseum (6-4) | 65-69 | Won 3 |
| » Starters: Moe Drabowsky vs Larry Sherry | Fifth | 10 out |
| » Major-league debuts: Ben Johnson (Cubs) |
| Monday, September 7 |
| » Lost to Dodgers (74-63), 7-1 | Los Angeles Memorial Coliseum (6-5) | 65-70 | |
| » Starters: Bob Anderson vs Johnny Podres | Fifth | 11 out |
| Wednesday, September 9 |
| » Lost to Reds (67-71), 4-2 | Wrigley Field (30-32) | 65-71 | Lost 2 |
| » Starters: Bob Purkey vs Glen Hobbie | Fifth | 12½ out |
| » Lost to Reds (68-71), 7-2 | Wrigley Field (30-33) | 65-72 | Lost 3 |
| » Starters: Jay Hook vs Dave Hillman | Fifth | 12½ out |
| » Major-league debuts: Cliff Cook and Buddy Gilbert (Reds) |
| Thursday, September 10 |
| » Lost to Reds (69-71), 10-4 | Wrigley Field (30-34) | 65-73 | Lost 4 |
| » Starters: Jim O'Toole vs Art Ceccarelli | Fifth | 12 out |
| » Defeated Reds (69-72), 6-3 | Wrigley Field (31-34) | 66-73 | |
| » Starters: Jim Bailey vs Ben Johnson | Fifth | 12 out |
| » Major-league debuts: Jim Bailey (Reds) |
| Friday, September 11 |
| » Defeated Cardinals (64-78), 2-1 | Wrigley Field (32-34) | 67-73 | Won 2 |
| » Starters: Bob Miller vs Bob Anderson | Sixth | 11 out |
| Saturday, September 12 |
| » Lost to Cardinals (65-78), 6-4 | Wrigley Field (32-35) | 67-74 | |
| » Starters: Bob Gibson vs Art Ceccarelli | Fifth | 12 out |
| Sunday, September 13 |
| » Defeated Cardinals (65-79), 8-0 | Wrigley Field (33-35) | 68-74 | |
| » Starters: Tom Hughes vs Glen Hobbie | Fifth | 12 out |
| » Major-league debuts: Tom Hughes (Cardinals) |
| Wednesday, September 16 |
| » Lost to Pirates (74-71), 3-2 | Wrigley Field (33-36) | 68-75 | |
| » Starters: Vern Law vs Bob Anderson | Sixth | 11½ out |
| » Defeated Pirates (74-72), 4-2 | Wrigley Field (34-36) | 69-75 | |
| » Starters: Bob Friend vs Ben Johnson | Sixth | 11½ out |
| Thursday, September 17 |
| » Lost to Phillies (61-85), 5-2 | Wrigley Field (34-37) | 69-76 | |
| » Starters: Robin Roberts vs Glen Hobbie | Fifth | 12½ out |
| Friday, September 18 |
| » Defeated Phillies (61-86), 5-4 | Wrigley Field (35-37) | 70-76 | |
| » Starters: Jim Owens vs Art Ceccarelli | Fifth | 12 out |
| Future Cub Ryne Sandberg is born in Spokane, WA. |
| Saturday, September 19 |
| » Lost to Cardinals (67-80), 2-1 | Sportsman's Park III (4-5) | 70-77 | |
| » Starters: Bob Anderson vs Bob Miller | Fifth | 11½ out |
| Sunday, September 20 |
| » Lost to Cardinals (68-80), 11-4 | Sportsman's Park III (4-6) | 70-78 | Lost 2 |
| » Starters: Moe Drabowsky vs Bob Blaylock | Sixth | 12½ out |
| Monday, September 21 |
| » Defeated Cardinals (68-81), 12-3 | Sportsman's Park III (5-6) | 71-78 | |
| » Starters: Glen Hobbie vs Tom Hughes | Fifth | 12 out |
| Tuesday, September 22 |
| » Defeated Giants (82-68), 5-4 | Wrigley Field (36-37) | 72-78 | Won 2 |
| » Starters: Jack Sanford vs Dave Hillman | Fifth | 12 out |
| Wednesday, September 23 |
| » Defeated Giants (82-69), 9-8 | Wrigley Field (37-37) | 73-78 | Won 3 |
| » Starters: Johnny Antonelli vs Bob Anderson | Fourth | 11 out |
| Friday, September 25 |
| » Lost to Dodgers (85-67), 5-4 | Wrigley Field (37-38) | 73-79 | |
| » Starters: Don Drysdale vs Glen Hobbie | Fifth | 12 out |
| Saturday, September 26 |
| » Defeated Dodgers (85-68), 12-2 | Wrigley Field (38-38) | 74-79 | |
| » |
