| Sunday, February 2 |
| Future Cub Pat Tabler is born in Hamilton, OH. |
| Monday, February 10 |
| Former Cub Elmer Jacobs dies in Salem, MO at the age of 66. |
| Friday, March 28 |
| Former Cub Chuck Klein dies in Indianapolis, IN at the age of 54. |
| Saturday, March 29 |
| Future Cub Domingo Ramos is born in Santiago, D.R. Former Cub Jimmy Archer dies in Milwaukee, WI at the age of 75. |
| Monday, April 14 |
| » Major-league debuts: Albie Pearson (Senators) |
| Tuesday, April 15 |
| » Defeated Cardinals (0-1), 4-0 | Sportsman's Park III (1-0) | 1-0 | |
| » Starters: Jim Brosnan vs Vinegar Bend Mizell | First | -- |
| » Major-league debuts: Phil Clark (Cardinals) Tony Taylor (Cubs) |
| Wednesday, April 16 |
| » Major-league debuts: Bob Schmidt (Giants) |
| Thursday, April 17 |
| » Defeated Cardinals (0-2), 4-3 | Sportsman's Park III (2-0) | 2-0 | Won 2 |
| » Starters: Glen Hobbie vs Lindy McDaniel | First | -- |
| Friday, April 18 |
| » Defeated Cardinals (0-3), 11-6 | Wrigley Field (1-0) | 3-0 | Won 3 |
| » Starters: Sam Jones vs Dick Drott | First | -- |
| » Major-league debuts: Bob Mabe (Cardinals) |
| Saturday, April 19 |
| » Defeated Cardinals (0-4), 6-3 | Wrigley Field (2-0) | 4-0 | Won 4 |
| » Starters: Vinegar Bend Mizell vs Taylor Phillips | First | -- |
| Sunday, April 20 |
| » Lost to Cardinals (1-4), 9-4 | Wrigley Field (2-1) | 4-1 | |
| » Starters: Herm Wehmeier vs Jim Brosnan | First | -- |
| Tuesday, April 22 |
| » Lost to Dodgers (3-4), 4-2 | Los Angeles Memorial Coliseum (0-1) | 4-2 | Lost 2 |
| » Starters: Glen Hobbie vs Johnny Podres | First | -- |
| Wednesday, April 23 |
| » Defeated Dodgers (3-5), 7-6 | Los Angeles Memorial Coliseum (1-1) | 5-2 | |
| » Starters: Dick Drott vs Carl Erskine | First | -- |
| Thursday, April 24 |
| » Defeated Dodgers (3-6), 15-2 | Los Angeles Memorial Coliseum (2-1) | 6-2 | Won 2 |
| » Starters: Gene Fodge vs Don Drysdale | First | -- |
| Friday, April 25 |
| » Lost to Giants (7-3), 2-0 | Seals Stadium (0-1) | 6-3 | |
| » Starters: Jim Brosnan vs Ramon Monzant | Second | ½ out |
| Future Cub Dave Owen is born in Cleburne, TX. |
| Saturday, April 26 |
| » Lost to Giants (8-3), 3-1 | Seals Stadium (0-2) | 6-4 | Lost 2 |
| » Starters: Glen Hobbie vs Johnny Antonelli | Third | 1½ out |
| Sunday, April 27 |
| » Defeated Giants (8-4), 5-4 | Seals Stadium (1-2) | 7-4 | |
| » Starters: Dick Drott vs Ruben Gomez | Second | ½ out |
| » Major-league debuts: Sammy Taylor (Cubs) |
| Tuesday, April 29 |
| » Lost to Braves (8-4), 8-4 | Wrigley Field (2-2) | 7-5 | |
| » Starters: Warren Spahn vs Gene Fodge | Third | 1 out |
| Wednesday, April 30 |
| » Defeated Braves (8-5), 8-2 | Wrigley Field (3-2) | 8-5 | |
| » Starters: Bob Buhl vs Jim Brosnan | Second | ½ out |
| » Major-league debuts: Carl Willey (Braves) |
| Thursday, May 1 |
| » Defeated Braves (8-6), 3-2 | Wrigley Field (4-2) | 9-5 | Won 2 |
| » Starters: Lew Burdette vs Glen Hobbie | First | -- |
| Friday, May 2 |
| » Defeated Braves (8-7), 8-7 | Wrigley Field (5-2) | 10-5 | Won 3 |
| » Starters: Gene Conley vs Dick Drott | First | -- |
| Saturday, May 3 |
| » Lost to Braves (9-7), 4-3 | Wrigley Field (5-3) | 10-6 | |
| » Starters: Bob Rush vs Taylor Phillips | First | -- |
| Sunday, May 4 |
| » Defeated Reds (7-6), 5-4 | Wrigley Field (6-3) | 11-6 | |
| » Starters: Bob Purkey vs Jim Brosnan | First | -- |
| » Lost to Reds (8-6), 3-2 | Wrigley Field (6-4) | 11-7 | |
| » Starters: Harvey Haddix vs Gene Fodge | First | -- |
| Monday, May 5 |
| Future Cub Dave Gumpert is born in South Haven, MI. |
| Tuesday, May 6 |
| » Defeated Reds (8-7), 4-0 | Wrigley Field (7-4) | 12-7 | |
| » Starters: Joe Nuxhall vs Glen Hobbie | First | -- |
| Wednesday, May 7 |
| » Defeated Reds (8-8), 5-1 | Wrigley Field (8-4) | 13-7 | Won 2 |
| » Starters: Brooks Lawrence vs Taylor Phillips | First | -- |
| Thursday, May 8 |
| » Lost to Reds (9-8), 10-8 | Wrigley Field (8-5) | 13-8 | |
| » Starters: Tom Acker vs Dick Drott | Second | 1 out |
| Friday, May 9 |
| » Lost to Cardinals (4-14), 3-2 | Sportsman's Park III (2-1) | 13-9 | Lost 2 |
| » Starters: Moe Drabowsky vs Sam Jones | Third | 1 out |
| Saturday, May 10 |
| » Lost to Cardinals (5-14), 3-1 | Sportsman's Park III (2-2) | 13-10 | Lost 3 |
| » Starters: Jim Brosnan vs Vinegar Bend Mizell | Fourth | 2 out |
| Sunday, May 11 |
| » Lost to Cardinals (6-14), 8-7 | Sportsman's Park III (2-3) | 13-11 | Lost 4 |
| » Starters: Glen Hobbie vs Von McDaniel | Third | 3½ out |
| » Lost to Cardinals (7-14), 6-5 | Sportsman's Park III (2-4) | 13-12 | Lost 5 |
| » Starters: Taylor Phillips vs Lindy McDaniel | Third | 3½ out |
| Monday, May 12 |
| » Lost to Cardinals (8-14), 6-4 | Wrigley Field (8-6) | 13-13 | Lost 6 |
| » Starters: Frank Barnes vs Glen Hobbie | Fourth | 4 out |
| Tuesday, May 13 |
| » Lost to Cardinals (9-14), 5-3 | Wrigley Field (8-7) | 13-14 | Lost 7 |
| » Starters: Sam Jones vs Moe Drabowsky | Fourth | 4½ out |
| Wednesday, May 14 |
| » Defeated Dodgers (9-18), 7-3 | Wrigley Field (9-7) | 14-14 | |
| » Starters: Carl Erskine vs Jim Brosnan | Fourth | 4 out |
| Former Cub Billy Clingman dies in Cincinnati, OH at the age of 89. |
| Thursday, May 15 |
| » Lost to Dodgers (10-18), 4-2 | Wrigley Field (9-8) | 14-15 | |
| » Starters: Clem Labine vs Dick Drott | Fourth | 4½ out |
| Friday, May 16 |
| » Defeated Giants (18-11), 6-5 | Wrigley Field (10-8) | 15-15 | |
| » Starters: Ramon Monzant vs Taylor Phillips | Fourth | 4 out |
| Saturday, May 17 |
| » Lost to Giants (19-11), 9-4 | Wrigley Field (10-9) | 15-16 | |
| » Starters: Ruben Gomez vs Glen Hobbie | Fourth | 5 out |
| Sunday, May 18 |
| » Lost to Giants (20-11), 7-3 | Wrigley Field (10-10) | 15-17 | Lost 2 |
| » Starters: Johnny Antonelli vs Moe Drabowsky | Fifth | 6½ out |
| » Lost to Giants (21-11), 4-0 | Wrigley Field (10-11) | 15-18 | Lost 3 |
| » Starters: Stu Miller vs Jim Brosnan | Fifth | 6½ out |
| Monday, May 19 |
| Future Cub Fritzie Connally is born in Bryan, TX. |
| Tuesday, May 20 |
| » Lost to Pirates (18-14), 12-3 | Forbes Field (0-1) | 15-19 | Lost 4 |
| » Starters: Dick Drott vs Bob Friend | Sixth | 7½ out |
| Wednesday, May 21 |
| » Defeated Pirates (18-15), 5-1 | Forbes Field (1-1) | 16-19 | |
| » Starters: Taylor Phillips vs Bob Porterfield | Fifth | 7½ out |
| Thursday, May 22 |
| » Defeated Phillies (15-18), 7-4 | Shibe Park (1-0) | 17-19 | Won 2 |
| » Starters: Moe Drabowsky vs Jack Sanford | Fourth | 6½ out |
| Friday, May 23 |
| » Defeated Phillies (15-19), 11-4 | Shibe Park (2-0) | 18-19 | Won 3 |
| » Starters: Glen Hobbie vs Ray Semproch | Fourth | 6½ out |
| Saturday, May 24 |
| » Lost to Phillies (16-19), 5-4 | Shibe Park (2-1) | 18-20 | |
| » Starters: Dick Drott vs Curt Simmons | Fourth | 6½ out |
| Sunday, May 25 |
| » Defeated Braves (20-13), 1-0 | County Stadium (1-0) | 19-20 | |
| » Starters: Taylor Phillips vs Bob Trowbridge | Fourth | 7½ out |
| » Lost to Braves (21-13), 5-2 | County Stadium (1-1) | 19-21 | |
| » Starters: Gene Fodge vs Bob Rush | Fourth | 7½ out |
| Monday, May 26 |
| » Lost to Braves (22-13), 4-3 | County Stadium (1-2) | 19-22 | Lost 2 |
| » Starters: Moe Drabowsky vs Lew Burdette | Fourth | 8 out |
| Tuesday, May 27 |
| » Lost to Reds (15-18), 4-3 | Crosley Field (0-1) | 19-23 | Lost 3 |
| » Starters: Glen Hobbie vs Brooks Lawrence | Sixth | 8 out |
| Wednesday, May 28 |
| » Defeated Reds (15-19), 6-4 | Crosley Field (1-1) | 20-23 | |
| » Starters: Dick Drott vs Bob Purkey | Fourth | 8 out |
| Friday, May 30 |
| » Defeated Dodgers (15-25), 3-2 | Wrigley Field (11-11) | 21-23 | Won 2 |
| » Starters: Johnny Podres vs Moe Drabowsky | Fourth | 6 out |
| » Defeated Dodgers (15-26), 10-8 | Wrigley Field (12-11) | 22-23 | Won 3 |
| » Starters: Don Newcombe vs Taylor Phillips | Fourth | 6 out |
| Saturday, May 31 |
| » Lost to Dodgers (16-26), 9-4 | Wrigley Field (12-12) | 22-24 | |
| » Starters: Carl Erskine vs Glen Hobbie | Fourth | 6 out |
| Sunday, June 1 |
| » Lost to Dodgers (17-26), 1-0 | Wrigley Field (12-13) | 22-25 | Lost 2 |
| » Starters: Stan Williams vs Dick Drott | Fifth | 7 out |
| Tuesday, June 3 |
| » Defeated Phillies (18-25), 12-4 | Wrigley Field (13-13) | 23-25 | |
| » Starters: Curt Simmons vs Taylor Phillips | Fifth | 6 out |
| Wednesday, June 4 |
| » Defeated Phillies (18-26), 11-5 | Wrigley Field (14-13) | 24-25 | Won 2 |
| » Starters: Robin Roberts vs Moe Drabowsky | Fourth | 6 out |
| Thursday, June 5 |
| » Lost to Phillies (19-26), 7-6 | Wrigley Field (14-14) | 24-26 | |
| » Starters: Jack Sanford vs Glen Hobbie | Sixth | 6 out |
| Friday, June 6 |
| » Defeated Pirates (23-25), 6-1 | Wrigley Field (15-14) | 25-26 | |
| » Starters: Vern Law vs Dick Drott | Fifth | 5 out |
| Saturday, June 7 |
| » Lost to Pirates (24-25), 8-6 | Wrigley Field (15-15) | 25-27 | |
| » Starters: Don Gross vs Taylor Phillips | Sixth | 6 out |
| Sunday, June 8 |
| » Defeated Pirates (24-26), 4-0 | Wrigley Field (16-15) | 26-27 | |
| » Starters: Ron Kline vs Moe Drabowsky | Fifth | 5 out |
| Tuesday, June 10 |
| » Defeated Braves (27-21), 9-6 | Wrigley Field (17-15) | 27-27 | Won 2 |
| » Starters: Warren Spahn vs Dick Drott | Fifth | 3½ out |
| Wednesday, June 11 |
| » Lost to Braves (28-21), 10-7 | Wrigley Field (17-16) | 27-28 | |
| » Starters: Bob Rush vs Taylor Phillips | Sixth | 4 out |
| Thursday, June 12 |
| » Lost to Braves (29-21), 5-4 | Wrigley Field (17-17) | 27-29 | Lost 2 |
| » Starters: Lew Burdette vs Moe Drabowsky | Sixth | 5 out |
| Saturday, June 14 |
| » Defeated Reds (25-24), 4-3 | Wrigley Field (18-17) | 28-29 | |
| » Starters: Bob Purkey vs John Briggs | Sixth | 4½ out |
| Sunday, June 15 |
| » Lost to Reds (26-24), 7-0 | Wrigley Field (18-18) | 28-30 | |
| » Starters: Harvey Haddix vs Taylor Phillips | Sixth | 6 out |
| » Lost to Reds (27-24), 4-2 | Wrigley Field (18-19) | 28-31 | Lost 2 |
| » Starters: Willard Schmidt vs Dick Drott | Sixth | 6 out |
| Tuesday, June 17 |
| » Lost to Braves (32-22), 6-3 | County Stadium (1-3) | 28-32 | Lost 3 |
| » Starters: Moe Drabowsky vs Lew Burdette | Sixth | 7 out |
| Thursday, June 19 |
| » Defeated Braves (32-23), 5-4 | County Stadium (2-3) | 29-32 | |
| » Starters: John Briggs vs Warren Spahn | Sixth | 6 out |
| Friday, June 20 |
| » Defeated Reds (28-27), 11-3 | Crosley Field (2-1) | 30-32 | Won 2 |
| » Starters: Taylor Phillips vs Bob Purkey | Sixth | 6 out |
| Saturday, June 21 |
| » Lost to Reds (29-27), 9-3 | Crosley Field (2-2) | 30-33 | |
| » Starters: Dick Drott vs Harvey Haddix | Sixth | 6 out |
| Sunday, June 22 |
| » Lost to Reds (30-27), 6-2 | Crosley Field (2-3) | 30-34 | Lost 2 |
| » Starters: Dick Ellsworth vs Joe Nuxhall | Sixth | 5½ out |
| » Defeated Reds (30-28), 8-6 | Crosley Field (3-3) | 31-34 | |
| » Starters: Moe Drabowsky vs Don Newcombe | Sixth | 5½ out |
| » Major-league debuts: Dick Ellsworth (Cubs) |
| Tuesday, June 24 |
| » Defeated Phillies (28-34), 3-0 | Shibe Park (3-1) | 32-34 | Won 2 |
| » Starters: John Briggs vs Jack Sanford | Sixth | 6 out |
| Wednesday, June 25 |
| » Lost to Phillies (29-34), 5-4 | Shibe Park (3-2) | 32-35 | |
| » Starters: Taylor Phillips vs Ray Semproch | Sixth | 6 out |
| Friday, June 27 |
| » Defeated Pirates (32-36), 3-1 | Forbes Field (2-1) | 33-35 | |
| » Starters: Moe Drabowsky vs Bob Friend | Fifth | 4½ out |
| Saturday, June 28 |
| » Lost to Pirates (33-36), 7-3 | Forbes Field (2-2) | 33-36 | |
| » Starters: Dick Drott vs Curt Raydon | Fifth | 5½ out |
| Sunday, June 29 |
| » Lost to Pirates (34-36), 4-3 | Forbes Field (2-3) | 33-37 | Lost 2 |
| » Starters: Taylor Phillips vs Ron Kline | Fifth | 6 out |
| » Defeated Pirates (34-37), 8-3 | Forbes Field (3-3) | 34-37 | |
| » Starters: John Briggs vs Don Gross | Fifth | 6 out |
| Tuesday, July 1 |
| » Defeated Giants (37-35), 9-5 | Wrigley Field (19-19) | 35-37 | Won 2 |
| » Starters: Johnny Antonelli vs Moe Drabowsky | Fifth | 6½ out |
| Wednesday, July 2 |
| » Lost to Giants (38-35), 5-2 | Wrigley Field (19-20) | 35-38 | |
| » Starters: Stu Miller vs Dick Drott | Fifth | 6½ out |
| Thursday, July 3 |
| » Defeated Giants (38-36), 4-3 | Seals Stadium (2-2) | 36-38 | |
| » Starters: Taylor Phillips vs Paul Giel | Fifth | 5½ out |
| Friday, July 4 |
| » Lost to Giants (39-36), 6-5 | Seals Stadium (2-3) | 36-39 | |
| » Starters: John Briggs vs Al Worthington | Sixth | 4½ out |
| » Defeated Giants (39-37), 6-1 | Seals Stadium (3-3) | 37-39 | |
| » Starters: Dave Hillman vs Johnny Antonelli | Sixth | 4½ out |
| Saturday, July 5 |
| » Defeated Dodgers (33-41), 7-1 | Los Angeles Memorial Coliseum (3-1) | 38-39 | Won 2 |
| » Starters: Moe Drabowsky vs Sandy Koufax | Fifth | 3½ out |
| Sunday, July 6 |
| » Defeated Dodgers (33-42), 6-2 | Los Angeles Memorial Coliseum (4-1) | 39-39 | Won 3 |
| » Starters: Dick Drott vs Don Drysdale | Fifth | 3½ out |
| Thursday, July 10 |
| » Defeated Pirates (36-42), 8-7 | Wrigley Field (20-20) | 40-39 | Won 4 |
| » Starters: Vern Law vs Taylor Phillips | Fifth | 3 out |
| Friday, July 11 |
| » Lost to Pirates (37-42), 7-2 | Wrigley Field (20-21) | 40-40 | |
| » Starters: Ron Kline vs Moe Drabowsky | Fifth | 4 out |
| Saturday, July 12 |
| » Lost to Phillies (39-38), 12-2 | Wrigley Field (20-22) | 40-41 | Lost 2 |
| » Starters: Ray Semproch vs Dick Drott | Sixth | 4 out |
| Sunday, July 13 |
| » Defeated Phillies (39-39), 3-2 | Wrigley Field (21-22) | 41-41 | |
| » Starters: Jack Meyer vs John Briggs | Fourth | 2½ out |
| » Defeated Phillies (39-40), 2-1 | Wrigley Field (22-22) | 42-41 | Won 2 |
| » Starters: Curt Simmons vs Dave Hillman | Fourth | 2½ out |
| Monday, July 14 |
| » Defeated Phillies (39-41), 11-10 | Wrigley Field (23-22) | 43-41 | Won 3 |
| » Starters: Don Cardwell vs Taylor Phillips | Fourth | 2½ out |
| Wednesday, July 16 |
| » Defeated Reds (38-43), 5-4 | Wrigley Field (24-22) | 44-41 | Won 4 |
| » Starters: Harvey Haddix vs Taylor Phillips | Third | 2½ out |
| » Defeated Reds (38-44), 7-5 | Wrigley Field (25-22) | 45-41 | Won 5 |
| » Starters: Brooks Lawrence vs Marcelino Solis | Third | 2½ out |
| Thursday, July 17 |
| » Lost to Reds (39-44), 3-2 | Wrigley Field (25-23) | 45-42 | |
| » Starters: Joe Nuxhall vs Dave Hillman | Third | 3½ out |
| Friday, July 18 |
| » Defeated Braves (46-37), 5-3 | Wrigley Field (26-23) | 46-42 | |
| » Starters: Carl Willey vs John Briggs | Third | 2½ out |
| Saturday, July 19 |
| » Lost to Braves (47-37), 3-2 | Wrigley Field (26-24) | 46-43 | |
| » Starters: Joey Jay vs Moe Drabowsky | Third | 3½ out |
| Sunday, July 20 |
| » Lost to Braves (48-37), 4-2 | Wrigley Field (26-25) | 46-44 | Lost 2 |
| » Starters: Warren Spahn vs Taylor Phillips | Third | 4½ out |
| Monday, July 21 |
| » Lost to Reds (42-46), 9-4 | Crosley Field (3-4) | 46-45 | Lost 3 |
| » Starters: Dick Drott vs Harvey Haddix | Third | 5 out |
| Wednesday, July 23 |
| » Lost to Reds (43-46), 6-5 | Crosley Field (3-5) | 46-46 | Lost 4 |
| » Starters: Dave Hillman vs Joe Nuxhall | Third | 6 out |
| » Major-league debuts: Lou Jackson (Cubs) |
| Thursday, July 24 |
| » Lost to Reds (44-46), 4-3 | Crosley Field (3-6) | 46-47 | Lost 5 |
| » Starters: John Briggs vs Brooks Lawrence | Third | 6 out |
| Friday, July 25 |
| » Defeated Braves (50-40), 5-4 | County Stadium (3-3) | 47-47 | |
| » Starters: Glen Hobbie vs Bob Trowbridge | Fourth | 6 out |
| » Lost to Braves (51-40), 4-1 | County Stadium (3-4) | 47-48 | |
| » Starters: Taylor Phillips vs Juan Pizarro | Fourth | 6 out |
| Saturday, July 26 |
| » Defeated Braves (51-41), 7-4 | County Stadium (4-4) | 48-48 | |
| » Starters: Dick Drott vs Lew Burdette | Second | 5 out |
| Sunday, July 27 |
| » Lost to Braves (52-41), 4-1 | County Stadium (4-5) | 48-49 | |
| » Starters: Dave Hillman vs Carl Willey | Fourth | 6 out |
| Tuesday, July 29 |
| » Lost to Pirates (48-48), 6-4 | Forbes Field (3-4) | 48-50 | Lost 2 |
| » Starters: John Briggs vs Bob Friend | Fifth | 6½ out |
| Wednesday, July 30 |
| » Lost to Pirates (49-48), 7-1 | Forbes Field (3-5) | 48-51 | Lost 3 |
| » Starters: Taylor Phillips vs George Witt | Fifth | 7 out |
| Future Cub Scott Fletcher is born in Fort Walton Beach, FL. |
| Thursday, July 31 |
| » Defeated Pirates (49-49), 5-4 | Forbes Field (4-5) | 49-51 | |
| » Starters: Marcelino Solis vs Curt Raydon | Fourth | 7 out |
| Friday, August 1 |
| » Lost to Phillies (47-50), 3-1 | Shibe Park (3-3) | 49-52 | |
| » Starters: Dave Hillman vs Robin Roberts | Sixth | 8 out |
| Saturday, August 2 |
| » Defeated Phillies (47-51), 6-5 | Shibe Park (4-3) | 50-52 | |
| » Starters: John Briggs vs Curt Simmons | Fifth | 8 out |
| Sunday, August 3 |
| » Lost to Phillies (48-51), 8-2 | Shibe Park (4-4) | 50-53 | |
| » Starters: Taylor Phillips vs Ray Semproch | Fifth | 9 out |
| » Defeated Phillies (48-52), 12-10 | Shibe Park (5-4) | 51-53 | |
| » Starters: Bob Anderson vs Jack Meyer | Fifth | 9 out |
| Monday, August 4 |
| » Lost to Giants (55-49), 6-4 | Wrigley Field (26-26) | 51-54 | |
| » Starters: Mike McCormick vs Dick Drott | Fifth | 9 out |
| Tuesday, August 5 |
| » Defeated Giants (55-50), 10-9 | Wrigley Field (27-26) | 52-54 | |
| » Starters: Stu Miller vs Dave Hillman | Fifth | 9 out |
| Wednesday, August 6 |
| » Lost to Dodgers (48-57), 5-2 | Wrigley Field (27-27) | 52-55 | |
| » Starters: Stan Williams vs John Briggs | Fifth | 10 out |
| Thursday, August 7 |
| » Lost to Dodgers (49-57), 3-1 | Wrigley Field (27-28) | 52-56 | Lost 2 |
| » Starters: Sandy Koufax vs Marcelino Solis | Sixth | 11 out |
| Friday, August 8 |
| » Lost to Cardinals (51-55), 6-3 | Wrigley Field (27-29) | 52-57 | Lost 3 |
| » Starters: Vinegar Bend Mizell vs Dick Drott | Sixth | 11 out |
| Saturday, August 9 |
| » Lost to Cardinals (52-55), 3-2 | Wrigley Field (27-30) | 52-58 | Lost 4 |
| » Starters: Sal Maglie vs Glen Hobbie | Seventh | 11 out |
| Sunday, August 10 |
| » Defeated Cardinals (52-56), 9-4 | Wrigley Field (28-30) | 53-58 | |
| » Starters: Billy Muffett vs John Briggs | Sixth | 12 out |
| » Lost to Cardinals (53-56), 6-2 | Wrigley Field (28-31) | 53-59 | |
| » Starters: Larry Jackson vs Dave Hillman | Sixth | 12 out |
| Tuesday, August 12 |
| » Defeated Dodgers (50-60), 9-3 | Los Angeles Memorial Coliseum (5-1) | 54-59 | |
| » Starters: Dick Drott vs Danny McDevitt | Sixth | 10½ out |
| Wednesday, August 13 |
| » Lost to Dodgers (51-60), 6-5 | Los Angeles Memorial Coliseum (5-2) | 54-60 | |
| » Starters: Glen Hobbie vs Sandy Koufax | Sixth | 12 out |
| Thursday, August 14 |
| » Lost to Dodgers (52-60), 7-3 | Los Angeles Memorial Coliseum (5-3) | 54-61 | Lost 2 |
| » Starters: John Briggs vs Don Drysdale | Sixth | 13 out |
| Friday, August 15 |
| » Defeated Giants (59-55), 3-1 | Seals Stadium (4-3) | 55-61 | |
| » Starters: Dave Hillman vs Stu Miller | Sixth | 13 out |
| Saturday, August 16 |
| » Lost to Giants (60-55), 7-4 | Seals Stadium (4-4) | 55-62 | |
| » Starters: Dick Drott vs Mike McCormick | Sixth | 14 out |
| Sunday, August 17 |
| » Lost to Giants (61-55), 8-6 | Seals Stadium (4-5) | 55-63 | Lost 2 |
| » Starters: Moe Drabowsky vs Ruben Gomez | Fifth | 15½ out |
| Tuesday, August 19 |
| » Lost to Pirates (63-55), 4-3 | Wrigley Field (28-32) | 55-64 | Lost 3 |
| » Starters: Curt Raydon vs Taylor Phillips | Sixth | 15 out |
| Wednesday, August 20 |
| » Lost to Pirates (64-55), 4-2 | Wrigley Field (28-33) | 55-65 | Lost 4 |
| » Starters: Ron Kline vs Dave Hillman | Seventh | 14½ out |
| » Defeated Pirates (64-56), 5-1 | Wrigley Field (29-33) | 56-65 | |
| » Starters: Bob Friend vs Dick Drott | Seventh | 14½ out |
| Thursday, August 21 |
| » Defeated Pirates (64-57), 5-3 | Wrigley Field (30-33) | 57-65 | Won 2 |
| » Starters: Vern Law vs Moe Drabowsky | Sixth | 14½ out |
| Friday, August 22 |
| » Lost to Pirates (65-57), 8-2 | Wrigley Field (30-34) | 57-66 | |
| » Starters: George Witt vs Marcelino Solis | Sixth | 15 out |
| Saturday, August 23 |
| » Lost to Pirates (66-57), 6-1 | Wrigley Field (30-35) | 57-67 | Lost 2 |
| » Starters: Bob Porterfield vs Taylor Phillips | Eighth | 15 out |
| Sunday, August 24 |
| » Lost to Phillies (56-64), 13-8 | Wrigley Field (30-36) | 57-68 | Lost 3 |
| » Starters: Ray Semproch vs Dick Drott | Eighth | 16½ out |
| » Lost to Phillies (57-64), 5-3 | Wrigley Field (30-37) | 57-69 | Lost 4 |
| » Starters: John Anderson vs Dave Hillman | Eighth | 16½ out |
| Tuesday, August 26 |
| » Lost to Phillies (58-64), 10-3 | Wrigley Field (30-38) | 57-70 | Lost 5 |
| » Starters: Robin Roberts vs Moe Drabowsky | Eighth | 18 out |
| Wednesday, August 27 |
| » Defeated Phillies (58-65), 5-2 | Wrigley Field (31-38) | 58-70 | |
| » Starters: Curt Simmons vs Bob Anderson | Eighth | 17 out |
| Thursday, August 28 |
| Former Cub Eddie Stack dies in Chicago, IL at the age of 71. |
| Friday, August 29 |
| » Lost to Cardinals (61-66), 7-5 | Sportsman's Park III (2-5) | 58-71 | |
| » Starters: Dick Drott vs Larry Jackson | Eighth | 17½ out |
| Saturday, August 30 |
| » Defeated Cardinals (61-67), 3-1 | Sportsman's Park III (3-5) | 59-71 | |
| » Starters: Dave Hillman vs Sam Jones | Seventh | 17½ out |
| Former Cub Frank Demaree dies in Los Angeles, CA at the age of 49. |
| Sunday, August 31 |
| » Defeated Cardinals (61-68), 8-5 | Sportsman's Park III (4-5) | 60-71 | Won 2 |
| » Starters: Moe Drabowsky vs Sal Maglie | Sixth | 17½ out |
| Monday, September 1 |
| » Lost to Braves (78-53), 2-1 | County Stadium (4-6) | 60-72 | |
| » Starters: Bob Anderson vs Bob Buhl | Seventh | 17½ out |
| » Defeated Braves (78-54), 9-3 | County Stadium (5-6) | 61-72 | |
| » Starters: Glen Hobbie vs Bob Rush | Seventh | 17½ out |
| Wednesday, September 3 |
| » Lost to Cardinals (64-69), 9-7 | Wrigley Field (31-39) | 61-73 | |
| » Starters: Larry Jackson vs Dick Drott | Seventh | 18½ out |
| Thursday, September 4 |
| » Lost to Cardinals (65-69), 4-2 | Wrigley Field (31-40) | 61-74 | Lost 2 |
| » Starters: Sam Jones vs Dave Hillman | Seventh | 19½ out |
| Former Cub Ward Miller dies in Dixon, IL at the age of 75. |
| Saturday, September 6 |
| » Defeated Giants (71-65), 6-3 | Wrigley Field (32-40) | 62-74 | |
| » Starters: Johnny Antonelli vs John Briggs | Seventh | 18 out |
| Sunday, September 7 |
| » Defeated Giants (71-66), 6-4 | Wrigley Field (33-40) | 63-74 | Won 2 |
| » Starters: Mike McCormick vs Bob Anderson | Seventh | 17 out |
| » Defeated Giants (71-67), 4-1 | Wrigley Field (34-40) | 64-74 | Won 3 |
| » Starters: Ruben Gomez vs Dick Drott | Seventh | 17 out |
| Tuesday, September 9 |
| » Lost to Cardinals (67-71), 8-7 | Sportsman's Park III (4-6) | 64-75 | |
| » Starters: Dave Hillman vs Sam Jones | Seventh | 18 out |
| Wednesday, September 10 |
| » Lost to Cardinals (68-71), 3-1 | Sportsman's Park III (4-7) | 64-76 | Lost 2 |
| » Starters: Taylor Phillips vs Vinegar Bend Mizell | Seventh | 19 out |
| » Major-league debuts: John Buzhardt (Cubs) |
| Thursday, September 11 |
| » Major-league debuts: Jimmie Coker (Phillies) |
| Friday, September 12 |
| » Defeated Reds (70-73), 7-5 | Crosley Field (4-6) | 65-76 | |
| » Starters: Dick Drott vs Joe Nuxhall | Seventh | 19 out |
| Saturday, September 13 |
| » Lost to Reds (71-73), 9-2 | Crosley Field (4-7) | 65-77 | |
| » Starters: John Briggs vs Alex Kellner | Seventh | 20 out |
| Sunday, September 14 |
| » Lost to Pirates (80-65), 5-4 | Forbes Field (4-6) | 65-78 | Lost 2 |
| » Starters: Bob Anderson vs Curt Raydon | Seventh | 20½ out |
| » Lost to Pirates (81-65), 6-2 | Forbes Field (4-7) | 65-79 | Lost 3 |
| » Starters: Taylor Phillips vs Bob Friend | Seventh | 20½ out |
| Tuesday, September 16 |
| » Defeated Phillies (63-82), 10-8 | Shibe Park (6-4) | 66-79 | |
| » Starters: Dick Drott vs Bob Conley | Seventh | 21 out |
| Wednesday, September 17 |
| » Defeated Phillies (63-83), 6-2 | Shibe Park (7-4) | 67-79 | Won 2 |
| » Starters: Bob Anderson vs Ray Semproch | Sixth | 20 out |
| Thursday, September 18 |
| » Major-league debuts: Ellis Burton (Cardinals) |
| Friday, September 19 |
| » Lost to Dodgers (68-79), 5-1 | Wrigley Field (34-41) | 67-80 | |
| » Starters: Ralph Mauriello vs John Briggs | Seventh | 20½ out |
| Saturday, September 20 |
| » Defeated Dodgers (68-80), 3-2 | Wrigley Field (35-41) | 68-80 | |
| » Starters: Don Drysdale vs John Buzhardt | Sixth | 20½ out |
| Sunday, September 21 |
| » Lost to Dodgers (69-80), 2-1 | Wrigley Field (35-42) | 68-81 | |
| » Starters: Sandy Koufax vs Bob Anderson | Seventh | 21½ out |
| Tuesday, September 23 |
| » Defeated Giants (78-72), 3-2 | Seals Stadium (5-5) | 69-81 | |
| » Starters: Dave Hillman vs Stu Miller | Sixth | 20½ out |
| Wednesday, September 24 |
| » Defeated Giants (78-73), 10-3 | Seals Stadium (6-5) | 70-81 | Won 2 |
| » Starters: John Briggs vs Ruben Gomez | Sixth | 20 out |
| Friday, September 26 |
| » Lost to Dodgers (71-81), 6-3 | Los Angeles Memorial Coliseum (5-4) | 70-82 | |
| » Starters: Bob Anderson vs Don Drysdale | Sixth | 20½ out |
| » Defeated Dodgers (71-82), 2-1 | Los Angeles Memorial Coliseum (6-4) | 71-82 | |
| » Starters: John Buzhardt vs Sandy Koufax | Sixth | 20½ out |
| Saturday, September 27 |
| » Defeated Dodgers (71-83), 7-4 | Los Angeles Memorial Coliseum (7-4) | 72-82 | Won 2 |
| » Starters: Dave Hillman vs Stan Williams | Six |
