| Tuesday, January 12 |
| Former Cub Jimmy Lavender dies in Cartersville, GA at the age of 76. |
| Thursday, March 17 |
| Former Cub Bob Thorpe dies in San Diego, CA at the age of 26. |
| Tuesday, April 12 |
| » Lost to Dodgers (1-0), 3-2 | Los Angeles Memorial Coliseum (0-1) | 0-1 | |
| » Starters: Bob Anderson vs Don Drysdale | Second | 1 out |
| Wednesday, April 13 |
| » Defeated Dodgers (1-1), 4-0 | Los Angeles Memorial Coliseum (1-1) | 1-1 | |
| » Starters: Glen Hobbie vs Larry Sherry | Third | 1 out |
| Thursday, April 14 |
| » Defeated Giants (2-1), 6-5 | Candlestick Park (1-0) | 2-1 | Won 2 |
| » Starters: Seth Morehead vs Jack Sanford | First | -- |
| Friday, April 15 |
| Future Cub Mike Diaz is born in San Francisco, CA. |
| Saturday, April 16 |
| » Lost to Giants (3-1), 6-1 | Candlestick Park (1-1) | 2-2 | |
| » Starters: Dick Drott vs Sam Jones | Third | 1 out |
| Sunday, April 17 |
| » Lost to Giants (4-1), 4-3 | Candlestick Park (1-2) | 2-3 | Lost 2 |
| » Starters: Bob Anderson vs Mike McCormick | Fourth | 2 out |
| Tuesday, April 19 |
| » Lost to Cardinals (1-5), 5-2 | Sportsman's Park III (0-1) | 2-4 | Lost 3 |
| » Starters: Seth Morehead vs Vinegar Bend Mizell | Sixth | 3 out |
| Former Cub Bob Osborn dies in Paris, AR at the age of 58. |
| Friday, April 22 |
| » Lost to Giants (6-2), 10-8 | Wrigley Field (0-1) | 2-5 | Lost 4 |
| » Starters: Sam Jones vs Glen Hobbie | Sixth | 3½ out |
| Saturday, April 23 |
| » Lost to Giants (7-2), 18-2 | Wrigley Field (0-2) | 2-6 | Lost 5 |
| » Starters: Jack Sanford vs Dick Drott | Eighth | 4½ out |
| Sunday, April 24 |
| » Defeated Giants (7-3), 9-4 | Wrigley Field (1-2) | 3-6 | |
| » Starters: Billy O'Dell vs Bob Anderson | Seventh | 4 out |
| Tuesday, April 26 |
| » Lost to Dodgers (6-5), 8-1 | Wrigley Field (1-3) | 3-7 | |
| » Starters: Don Drysdale vs Glen Hobbie | Seventh | 4½ out |
| Wednesday, April 27 |
| » Lost to Dodgers (7-5), 9-4 | Wrigley Field (1-4) | 3-8 | Lost 2 |
| » Starters: Roger Craig vs Dick Drott | Eighth | 5½ out |
| Friday, April 29 |
| » Lost to Cardinals (6-6), 16-6 | Sportsman's Park III (0-2) | 3-9 | Lost 3 |
| » Starters: Seth Morehead vs Bob Miller | Eighth | 6½ out |
| Saturday, April 30 |
| » Lost to Cardinals (7-6), 5-4 | Sportsman's Park III (0-3) | 3-10 | Lost 4 |
| » Starters: Bob Anderson vs Vinegar Bend Mizell | Eighth | 7½ out |
| Sunday, May 1 |
| » Defeated Cardinals (7-7), 5-4 | Sportsman's Park III (1-3) | 4-10 | |
| » Starters: Glen Hobbie vs Larry Jackson | Seventh | 7½ out |
| Monday, May 2 |
| » Defeated Phillies (5-11), 8-7 | Wrigley Field (2-4) | 5-10 | Won 2 |
| » Starters: Robin Roberts vs Dick Drott | Sixth | 6½ out |
| Tuesday, May 3 |
| » Lost to Phillies (6-11), 10-9 | Wrigley Field (2-5) | 5-11 | |
| » Starters: Gene Conley vs Art Ceccarelli | Seventh | 7 out |
| Wednesday, May 4 |
| » Defeated Pirates (12-5), 5-1 | Wrigley Field (3-5) | 6-11 | |
| » Starters: Bob Friend vs Dick Ellsworth | Seventh | 6 out |
| Thursday, May 5 |
| » Lost to Pirates (13-5), 9-7 | Wrigley Field (3-6) | 6-12 | |
| » Manager: Lou Boudreau |
| » Starters: George Witt vs Seth Morehead | Eighth | 7 out |
| Thursday, May 12 |
| » Lost to Reds (12-11), 14-1 | Wrigley Field (3-7) | 6-13 | Lost 2 |
| » Starters: Bob Purkey vs Bob Anderson | Eighth | 8½ out |
| Friday, May 13 |
| » Defeated Cardinals (9-14), 4-1 | Wrigley Field (4-7) | 7-13 | |
| » Starters: Ron Kline vs Glen Hobbie | Seventh | 8½ out |
| Saturday, May 14 |
| » Defeated Cardinals (9-15), 4-0 | Wrigley Field (5-7) | 8-13 | Won 2 |
| » Starters: Frank Barnes vs Dick Ellsworth | Sixth | 7½ out |
| Sunday, May 15 |
| » Lost to Cardinals (10-15), 6-1 | Wrigley Field (5-8) | 8-14 | |
| » Starters: Larry Jackson vs Dick Drott | Sixth | 8 out |
| » Defeated Cardinals (10-16), 4-0 | Wrigley Field (6-8) | 9-14 | |
| » Starters: Lindy McDaniel vs Don Cardwell | Sixth | 8 out |
| Tuesday, May 17 |
| » Lost to Pirates (19-10), 11-6 | Forbes Field (0-1) | 9-15 | |
| » Starters: Glen Hobbie vs Bob Friend | Seventh | 8½ out |
| Thursday, May 19 |
| » Defeated Phillies (11-20), 4-2 | Shibe Park (1-0) | 10-15 | |
| » Starters: Bob Anderson vs Robin Roberts | Sixth | 8 out |
| Saturday, May 21 |
| » Lost to Braves (14-11), 4-2 | County Stadium (0-1) | 10-16 | |
| » Starters: Dick Ellsworth vs Joey Jay | Seventh | 8½ out |
| Sunday, May 22 |
| » Lost to Braves (15-11), 3-1 | County Stadium (0-2) | 10-17 | Lost 2 |
| » Starters: Glen Hobbie vs Juan Pizarro | Sixth | 9½ out |
| Monday, May 23 |
| » Defeated Reds (18-18), 7-6 | Crosley Field (1-0) | 11-17 | |
| » Starters: Bob Anderson vs Cal McLish | Seventh | 8½ out |
| Wednesday, May 25 |
| » Lost to Reds (19-18), 7-4 | Crosley Field (1-1) | 11-18 | |
| » Starters: Don Cardwell vs Jim O'Toole | Seventh | 9 out |
| Friday, May 27 |
| » Lost to Dodgers (18-19), 5-3 | Wrigley Field (6-9) | 11-19 | Lost 2 |
| » Starters: Stan Williams vs Glen Hobbie | Seventh | 9½ out |
| Saturday, May 28 |
| » Defeated Dodgers (18-20), 4-3 | Wrigley Field (7-9) | 12-19 | |
| » Starters: Sandy Koufax vs Dick Ellsworth | Seventh | 9½ out |
| Sunday, May 29 |
| » Lost to Dodgers (19-20), 4-0 | Wrigley Field (7-10) | 12-20 | |
| » Starters: Johnny Podres vs Don Cardwell | Sixth | 9½ out |
| Monday, May 30 |
| » Defeated Giants (25-15), 2-1 | Candlestick Park (2-2) | 13-20 | |
| » Starters: Bob Anderson vs Mike McCormick | Seventh | 10 out |
| » Lost to Giants (26-15), 5-4 | Candlestick Park (2-3) | 13-21 | |
| » Starters: Dick Drott vs Jack Sanford | Seventh | 10 out |
| Tuesday, May 31 |
| » Defeated Giants (26-16), 9-1 | Candlestick Park (3-3) | 14-21 | |
| » Starters: Glen Hobbie vs Johnny Antonelli | Seventh | 10 out |
| Wednesday, June 1 |
| » Lost to Giants (27-16), 2-1 | Candlestick Park (3-4) | 14-22 | |
| » Starters: Dick Ellsworth vs Sam Jones | Seventh | 11 out |
| Thursday, June 2 |
| » Defeated Dodgers (20-23), 10-8 | Los Angeles Memorial Coliseum (2-1) | 15-22 | |
| » Starters: Don Cardwell vs Don Drysdale | Seventh | 10½ out |
| Friday, June 3 |
| » Defeated Dodgers (20-24), 6-5 | Los Angeles Memorial Coliseum (3-1) | 16-22 | Won 2 |
| » Starters: Bob Anderson vs Johnny Podres | Seventh | 10½ out |
| Saturday, June 4 |
| » Lost to Dodgers (21-24), 12-6 | Los Angeles Memorial Coliseum (3-2) | 16-23 | |
| » Starters: Glen Hobbie vs Stan Williams | Seventh | 11 out |
| Sunday, June 5 |
| » Defeated Dodgers (21-25), 12-8 | Los Angeles Memorial Coliseum (4-2) | 17-23 | |
| » Starters: Mark Freeman vs Sandy Koufax | Seventh | 9½ out |
| Tuesday, June 7 |
| » Defeated Pirates (29-17), 13-2 | Wrigley Field (8-10) | 18-23 | Won 2 |
| » Starters: Vern Law vs Dick Ellsworth | Seventh | 8½ out |
| Wednesday, June 8 |
| » Lost to Pirates (30-17), 5-3 | Wrigley Field (8-11) | 18-24 | |
| » Starters: Vinegar Bend Mizell vs Bob Anderson | Sixth | 9½ out |
| Thursday, June 9 |
| » Lost to Pirates (31-17), 11-3 | Wrigley Field (8-12) | 18-25 | Lost 2 |
| » Starters: Bob Friend vs Glen Hobbie | Seventh | 10½ out |
| Friday, June 10 |
| » Defeated Phillies (18-32), 6-1 | Wrigley Field (9-12) | 19-25 | |
| » Starters: Jim Owens vs Mark Freeman | Seventh | 9½ out |
| Saturday, June 11 |
| » Lost to Phillies (19-32), 7-1 | Wrigley Field (9-13) | 19-26 | |
| » Starters: Chris Short vs Dick Ellsworth | Seventh | 9½ out |
| Sunday, June 12 |
| » Defeated Phillies (19-33), 8-7 | Wrigley Field (10-13) | 20-26 | |
| » Starters: John Buzhardt vs Moe Drabowsky | Seventh | 9 out |
| Tuesday, June 14 |
| » Defeated Braves (25-21), 3-2 | County Stadium (1-2) | 21-26 | Won 2 |
| » Starters: Glen Hobbie vs Bob Buhl | Seventh | 9 out |
| Wednesday, June 15 |
| » Lost to Braves (26-21), 5-4 | County Stadium (1-3) | 21-27 | |
| » Starters: Dick Ellsworth vs Warren Spahn | Seventh | 9½ out |
| » Defeated Braves (26-22), 8-5 | County Stadium (2-3) | 22-27 | |
| » Starters: Bob Anderson vs Carl Willey | Seventh | 9½ out |
| Thursday, June 16 |
| » Lost to Braves (27-22), 10-7 | County Stadium (2-4) | 22-28 | |
| » Starters: Mark Freeman vs Juan Pizarro | Seventh | 10½ out |
| Friday, June 17 |
| » Defeated Reds (26-31), 6-4 | Crosley Field (2-1) | 23-28 | |
| » Starters: Moe Drabowsky vs Don Newcombe | Seventh | 10½ out |
| Saturday, June 18 |
| » Lost to Reds (27-31), 7-1 | Crosley Field (2-2) | 23-29 | |
| » Starters: Seth Morehead vs Jay Hook | Seventh | 11½ out |
| » Major-league debuts: Danny Murphy (Cubs) |
| Sunday, June 19 |
| » Lost to Reds (28-31), 4-3 | Crosley Field (2-3) | 23-30 | Lost 2 |
| » Starters: Glen Hobbie vs Jim O'Toole | Seventh | 12 out |
| » Lost to Reds (29-31), 7-5 | Crosley Field (2-4) | 23-31 | Lost 3 |
| » Starters: Dick Ellsworth vs Cal McLish | Seventh | 12 out |
| Tuesday, June 21 |
| » Lost to Phillies (22-37), 7-6 | Shibe Park (1-1) | 23-32 | Lost 4 |
| » Starters: Don Cardwell vs Jim Owens | Seventh | 13½ out |
| » Lost to Phillies (23-37), 7-6 | Shibe Park (1-2) | 23-33 | Lost 5 |
| » Starters: Mark Freeman vs John Buzhardt | Seventh | 13½ out |
| Wednesday, June 22 |
| » Lost to Phillies (24-37), 6-3 | Shibe Park (1-3) | 23-34 | Lost 6 |
| » Starters: Bob Anderson vs Chris Short | Seventh | 14½ out |
| Thursday, June 23 |
| » Lost to Phillies (25-37), 4-3 | Shibe Park (1-4) | 23-35 | Lost 7 |
| » Starters: Glen Hobbie vs Dallas Green | Seventh | 14½ out |
| Friday, June 24 |
| » Lost to Pirates (40-22), 4-1 | Forbes Field (0-2) | 23-36 | Lost 8 |
| » Starters: Dick Ellsworth vs Vinegar Bend Mizell | Seventh | 15½ out |
| Saturday, June 25 |
| » Lost to Pirates (41-22), 7-6 | Forbes Field (0-3) | 23-37 | Lost 9 |
| » Starters: Moe Drabowsky vs Joe Gibbon | Eighth | 16½ out |
| Sunday, June 26 |
| » Defeated Pirates (41-23), 7-6 | Forbes Field (1-3) | 24-37 | |
| » Starters: Mark Freeman vs Bob Friend | Eighth | 14½ out |
| » Defeated Pirates (41-24), 7-5 | Forbes Field (2-3) | 25-37 | Won 2 |
| » Starters: Don Cardwell vs Vern Law | Eighth | 14½ out |
| » Major-league debuts: Ron Santo (Cubs) |
| Tuesday, June 28 |
| » Lost to Braves (37-25), 5-3 | Wrigley Field (10-14) | 25-38 | |
| » Starters: Warren Spahn vs Glen Hobbie | Eighth | 15 out |
| Wednesday, June 29 |
| » Defeated Braves (37-26), 3-2 | Wrigley Field (11-14) | 26-38 | |
| » Starters: Bob Buhl vs Dick Ellsworth | Seventh | 15 out |
| » Lost to Braves (38-26), 3-1 | Wrigley Field (11-15) | 26-39 | |
| » Starters: Joey Jay vs Bob Anderson | Seventh | 15 out |
| Thursday, June 30 |
| » Defeated Braves (38-27), 11-5 | Wrigley Field (12-15) | 27-39 | |
| » Starters: Lew Burdette vs Don Cardwell | Sixth | 14½ out |
| Friday, July 1 |
| » Lost to Reds (33-35), 5-3 | Wrigley Field (12-16) | 27-40 | |
| » Starters: Don Newcombe vs Mark Freeman | Seventh | 15½ out |
| Saturday, July 2 |
| » Lost to Reds (34-35), 13-8 | Wrigley Field (12-17) | 27-41 | Lost 2 |
| » Starters: Bob Purkey vs Dick Drott | Eighth | 15½ out |
| Sunday, July 3 |
| » Defeated Reds (34-36), 7-5 | Wrigley Field (13-17) | 28-41 | |
| » Starters: Jim O'Toole vs Glen Hobbie | Seventh | 14½ out |
| Former Cub Bill Killefer dies in Elsmere, DE at the age of 73. |
| Monday, July 4 |
| » Lost to Giants (39-33), 4-0 | Wrigley Field (13-18) | 28-42 | |
| » Starters: Jack Sanford vs Dick Ellsworth | Eighth | 15 out |
| » Tied Giants, 1-1 | Wrigley Field (13-18) | 28-42 | |
| » Starters: Johnny Antonelli vs Bob Anderson | Eighth | 15 out |
| Tuesday, July 5 |
| » Lost to Cardinals (38-37), 3-2 | Wrigley Field (13-19) | 28-43 | Lost 2 |
| » Starters: Curt Simmons vs Don Cardwell | Eighth | 16 out |
| Wednesday, July 6 |
| » Defeated Cardinals (38-38), 10-1 | Wrigley Field (14-19) | 29-43 | |
| » Starters: Bob Gibson vs Glen Hobbie | Eighth | 16 out |
| » Major-league debuts: Ed Bauta (Cardinals) |
| Thursday, July 7 |
| » Lost to Dodgers (39-37), 7-1 | Los Angeles Memorial Coliseum (4-3) | 29-44 | |
| » Starters: Mark Freeman vs Don Drysdale | Eighth | 17 out |
| Friday, July 8 |
| » Lost to Dodgers (40-37), 5-3 | Los Angeles Memorial Coliseum (4-4) | 29-45 | Lost 2 |
| » Starters: Bob Anderson vs Roger Craig | Eighth | 17½ out |
| Saturday, July 9 |
| » Defeated Giants (39-38), 7-6 | Candlestick Park (4-4) | 30-45 | |
| » Starters: Dick Ellsworth vs Mike McCormick | Eighth | 16½ out |
| Sunday, July 10 |
| » Lost to Giants (40-38), 5-3 | Candlestick Park (4-5) | 30-46 | |
| » Starters: Don Cardwell vs Billy O'Dell | Eighth | 17½ out |
| Friday, July 15 |
| » Lost to Cardinals (42-39), 6-0 | Sportsman's Park III (1-4) | 30-47 | Lost 2 |
| » Starters: Don Cardwell vs Ernie Broglio | Eighth | 17 out |
| Saturday, July 16 |
| » Lost to Cardinals (43-39), 2-1 | Sportsman's Park III (1-5) | 30-48 | Lost 3 |
| » Starters: Glen Hobbie vs Curt Simmons | Eighth | 18 out |
| Sunday, July 17 |
| » Lost to Cardinals (44-39), 6-0 | Sportsman's Park III (1-6) | 30-49 | Lost 4 |
| » Starters: Dick Ellsworth vs Larry Jackson | Eighth | 19 out |
| » Lost to Cardinals (45-39), 8-1 | Sportsman's Park III (1-7) | 30-50 | Lost 5 |
| » Starters: Bob Anderson vs Ray Sadecki | Eighth | 19 out |
| » Major-league debuts: Jim Brewer (Cubs) |
| Tuesday, July 19 |
| » Lost to Reds (39-44), 4-1 | Crosley Field (2-5) | 30-51 | Lost 6 |
| » Starters: Don Cardwell vs Jim O'Toole | Eighth | 19 out |
| Wednesday, July 20 |
| » Defeated Reds (39-45), 4-0 | Crosley Field (3-5) | 31-51 | |
| » Starters: Glen Hobbie vs Jay Hook | Eighth | 18½ out |
| » Lost to Reds (40-45), 4-3 | Crosley Field (3-6) | 31-52 | |
| » Starters: Jim Brewer vs Don Newcombe | Eighth | 18½ out |
| Thursday, July 21 |
| » Defeated Reds (40-46), 8-1 | Crosley Field (4-6) | 32-52 | |
| » Starters: Bob Anderson vs Bob Purkey | Eighth | 18½ out |
| Friday, July 22 |
| » Defeated Braves (49-36), 8-7 | Wrigley Field (15-19) | 33-52 | Won 2 |
| » Starters: Lew Burdette vs Mark Freeman | Eighth | 18½ out |
| Saturday, July 23 |
| » Lost to Braves (50-36), 3-0 | Wrigley Field (15-20) | 33-53 | |
| » Starters: Juan Pizarro vs Don Cardwell | Eighth | 18½ out |
| Sunday, July 24 |
| » Lost to Braves (51-36), 7-5 | Wrigley Field (15-21) | 33-54 | Lost 2 |
| » Starters: Warren Spahn vs Glen Hobbie | Eighth | 19 out |
| » Lost to Braves (52-36), 1-0 | Wrigley Field (15-22) | 33-55 | Lost 3 |
| » Starters: Bob Buhl vs Jim Brewer | Eighth | 19 out |
| Monday, July 25 |
| » Lost to Reds (41-49), 6-5 | Wrigley Field (15-23) | 33-56 | Lost 4 |
| » Starters: Don Newcombe vs Bob Anderson | Eighth | 20 out |
| Tuesday, July 26 |
| » Lost to Phillies (36-55), 4-3 | Wrigley Field (15-24) | 33-57 | Lost 5 |
| » Starters: Robin Roberts vs Glen Hobbie | Eighth | 21 out |
| Wednesday, July 27 |
| » Lost to Phillies (37-55), 7-5 | Wrigley Field (15-25) | 33-58 | Lost 6 |
| » Starters: Gene Conley vs Don Cardwell | Eighth | 22 out |
| Thursday, July 28 |
| » Lost to Phillies (38-55), 3-2 | Wrigley Field (15-26) | 33-59 | Lost 7 |
| » Starters: Dallas Green vs Dick Ellsworth | Eighth | 22½ out |
| Future Cub Carmelo Martinez is born in Dorado, P.R. |
| Friday, July 29 |
| » Lost to Pirates (57-37), 4-0 | Wrigley Field (15-27) | 33-60 | Lost 8 |
| » Starters: Vinegar Bend Mizell vs Jim Brewer | Eighth | 23½ out |
| Saturday, July 30 |
| » Defeated Pirates (57-38), 6-1 | Wrigley Field (16-27) | 34-60 | |
| » Starters: Bob Friend vs Glen Hobbie | Eighth | 22½ out |
| Sunday, July 31 |
| » Defeated Pirates (57-39), 6-2 | Wrigley Field (17-27) | 35-60 | Won 2 |
| » Starters: Harvey Haddix vs Don Cardwell | Eighth | 21½ out |
| Tuesday, August 2 |
| » Defeated Reds (42-55), 5-3 | Wrigley Field (18-27) | 36-60 | Won 3 |
| » Starters: Jim Maloney vs Bob Anderson | Eighth | 21½ out |
| Wednesday, August 3 |
| » Lost to Reds (43-55), 7-3 | Wrigley Field (18-28) | 36-61 | |
| » Starters: Jim O'Toole vs Glen Hobbie | Eighth | 21 out |
| » Defeated Reds (43-56), 4-2 | Wrigley Field (19-28) | 37-61 | |
| » Starters: Jay Hook vs Dick Ellsworth | Eighth | 21 out |
| » Major-league debuts: Joe Azcue (Reds) |
| Thursday, August 4 |
| » Defeated Reds (43-57), 5-3 | Wrigley Field (20-28) | 38-61 | Won 2 |
| » Starters: Cal McLish vs Jim Brewer | Eighth | 21 out |
| Friday, August 5 |
| » Lost to Braves (55-43), 10-2 | County Stadium (2-5) | 38-62 | |
| » Starters: Don Cardwell vs Lew Burdette | Eighth | 22 out |
| Saturday, August 6 |
| » Defeated Braves (55-44), 3-2 | County Stadium (3-5) | 39-62 | |
| » Starters: Bob Anderson vs Juan Pizarro | Eighth | 22 out |
| Sunday, August 7 |
| » Lost to Braves (56-44), 5-4 | County Stadium (3-6) | 39-63 | |
| » Starters: Glen Hobbie vs Warren Spahn | Eighth | 23½ out |
| Tuesday, August 9 |
| » Lost to Pirates (64-40), 7-1 | Forbes Field (2-4) | 39-64 | Lost 2 |
| » Starters: Moe Drabowsky vs Vinegar Bend Mizell | Eighth | 24½ out |
| Wednesday, August 10 |
| » Lost to Pirates (65-40), 3-1 | Forbes Field (2-5) | 39-65 | Lost 3 |
| » Starters: Don Cardwell vs Vern Law | Seventh | 25½ out |
| Friday, August 12 |
| » Lost to Phillies (43-65), 10-6 | Shibe Park (1-5) | 39-66 | Lost 4 |
| » Starters: Glen Hobbie vs Robin Roberts | Seventh | 25 out |
| Saturday, August 13 |
| » Defeated Phillies (43-66), 4-2 | Shibe Park (2-5) | 40-66 | |
| » Starters: Bob Anderson vs John Buzhardt | Eighth | 25 out |
| Sunday, August 14 |
| » Defeated Phillies (43-67), 2-1 | Shibe Park (3-5) | 41-66 | Won 2 |
| » Starters: Dick Ellsworth vs Gene Conley | Seventh | 25 out |
| » Defeated Phillies (43-68), 7-3 | Shibe Park (4-5) | 42-66 | Won 3 |
| » Starters: Moe Drabowsky vs Dallas Green | Seventh | 25 out |
| Tuesday, August 16 |
| » Lost to Dodgers (60-49), 7-5 | Wrigley Field (20-29) | 42-67 | |
| » Starters: Sandy Koufax vs Don Cardwell | Eighth | 26 out |
| Wednesday, August 17 |
| » Defeated Dodgers (60-50), 1-0 | Wrigley Field (21-29) | 43-67 | |
| » Starters: Don Drysdale vs Glen Hobbie | Seventh | 26 out |
| Thursday, August 18 |
| » Lost to Dodgers (61-50), 4-3 | Wrigley Field (21-30) | 43-68 | |
| » Starters: Roger Craig vs Bob Anderson | Seventh | 27 out |
| Friday, August 19 |
| » Lost to Giants (56-55), 2-1 | Wrigley Field (21-31) | 43-69 | Lost 2 |
| » Starters: Mike McCormick vs Dick Ellsworth | Eighth | 27 out |
| Saturday, August 20 |
| » Defeated Giants (56-56), 9-5 | Wrigley Field (22-31) | 44-69 | |
| » Starters: Sam Jones vs Moe Drabowsky | Seventh | 27 out |
| Sunday, August 21 |
| » Defeated Giants (56-57), 5-3 | Wrigley Field (23-31) | 45-69 | Won 2 |
| » Starters: Billy O'Dell vs Glen Hobbie | Seventh | 26½ out |
| » Lost to Giants (57-57), 5-3 | Wrigley Field (23-32) | 45-70 | |
| » Starters: Georges Maranda vs Don Cardwell | Seventh | 26½ out |
| Monday, August 22 |
| » Defeated Reds (54-66), 6-3 | Wrigley Field (24-32) | 46-70 | |
| » Starters: Cal McLish vs Bob Anderson | Seventh | 26 out |
| Tuesday, August 23 |
| » Lost to Pirates (74-45), 8-3 | Wrigley Field (24-33) | 46-71 | |
| » Starters: Harvey Haddix vs Dick Ellsworth | Seventh | 27 out |
| Wednesday, August 24 |
| » Lost to Pirates (75-45), 10-6 | Wrigley Field (24-34) | 46-72 | Lost 2 |
| » Starters: Vern Law vs Don Cardwell | Seventh | 28 out |
| Thursday, August 25 |
| » Defeated Pirates (75-46), 2-1 | Wrigley Field (25-34) | 47-72 | |
| » Starters: Vinegar Bend Mizell vs Glen Hobbie | Seventh | 27 out |
| Friday, August 26 |
| » Lost to Phillies (47-75), 4-2 | Wrigley Field (25-35) | 47-73 | |
| » Starters: Robin Roberts vs Bob Anderson | Seventh | 27 out |
| Saturday, August 27 |
| » Defeated Phillies (47-76), 5-4 | Wrigley Field (26-35) | 48-73 | |
| » Starters: John Buzhardt vs Dick Ellsworth | Seventh | 26 out |
| Sunday, August 28 |
| » Defeated Phillies (47-77), 8-6 | Wrigley Field (27-35) | 49-73 | Won 2 |
| » Starters: Gene Conley vs Don Cardwell | Seventh | 25 out |
| Tuesday, August 30 |
| » Defeated Reds (56-71), 5-4 | Wrigley Field (28-35) | 50-73 | Won 3 |
| » Starters: Jim O'Toole vs Glen Hobbie | Seventh | 25½ out |
| Wednesday, August 31 |
| » Defeated Braves (69-55), 5-4 | Wrigley Field (29-35) | 51-73 | Won 4 |
| » Starters: Lew Burdette vs Dick Ellsworth | Seventh | 26 out |
| » Lost to Braves (70-55), 11-7 | Wrigley Field (29-36) | 51-74 | |
| » Starters: Carl Willey vs Bob Anderson | Seventh | 26 out |
| Thursday, September 1 |
| » Lost to Braves (71-55), 10-1 | Wrigley Field (29-37) | 51-75 | Lost 2 |
| » Starters: Bob Buhl vs Dick Drott | Seventh | 27 out |
| Friday, September 2 |
| » Defeated Cardinals (71-57), 10-4 | Sportsman's Park III (2-7) | 52-75 | |
| » Starters: Don Cardwell vs Larry Jackson | Seventh | 26½ out |
| Saturday, September 3 |
| » Lost to Cardinals (72-57), 4-0 | Sportsman's Park III (2-8) | 52-76 | |
| » Starters: Glen Hobbie vs Ernie Broglio | Seventh | 26½ out |
| Sunday, September 4 |
| » Lost to Cardinals (73-57), 4-3 | Sportsman's Park III (2-9) | 52-77 | Lost 2 |
| » Starters: Dick Ellsworth vs Curt Simmons | Seventh | 27½ out |
| Monday, September 5 |
| » Lost to Cardinals (74-57), 2-1 | Wrigley Field (29-38) | 52-78 | Lost 3 |
| » Starters: Larry Jackson vs Bob Anderson | Sixth | 28 out |
| » Tied Cardinals, 4-4 | Wrigley Field (29-38) | 52-78 | |
| » Starters: Ray Sadecki vs Moe Drabowsky | Sixth | 28 out |
| Future Cub Candy Maldonado is born in Humacao, P.R. |
| Wednesday, September 7 |
| » Lost to Phillies (50-83), 2-0 | Shibe Park (4-6) | 52-79 | Lost 4 |
| » Starters: Don Cardwell vs Gene Conley | Seventh | 28½ out |
| Thursday, September 8 |
| » Defeated Phillies (50-84), 2-1 | Shibe Park (5-6) | 53-79 | |
| » Starters: Glen Hobbie vs Art Mahaffey | Seventh | 28 out |
| Friday, September 9 |
| » Lost to Pirates (83-52), 4-3 | Forbes Field (2-6) | 53-80 | |
| » Starters: Dick Ellsworth vs Vinegar Bend Mizell | Seventh | 29 out |
| » Major-league debuts: Nelson Mathews (Cubs) |
| Saturday, September 10 |
| » Lost to Pirates (84-52), 4-1 | Forbes Field (2-7) | 53-81 | Lost 2 |
| » Starters: Bob Anderson vs Bob Friend | Seventh | 30 out |
| Tuesday, September 13 |
| » Lost to Reds (64-77), 8-6 | Crosley Field (4-7) | 53-82 | Lost 3 |
| » Starters: Dick Burwell vs Bob Purkey | Seventh | 30½ out |
| Wednesday, September 14 |
| » Lost to Braves (79-61), 10-2 | County Stadium (3-7) | 53-83 | Lost 4 |
| » Starters: Don Cardwell vs Joey Jay | Seventh | 30½ out |
| Thursday, September 15 |
| » Lost to Braves (80-61), 3-1 | County Stadium (3-8) | 53-84 | Lost 5 |
| » Starters: Glen Hobbie vs Lew Burdette | Seventh | 31½ out |
| Friday, September 16 |
| » Lost to Dodgers (77-64), 5-4 | Wrigley Field (29-39) | 53-85 | Lost 6 |
| » Starters: Don Drysdale vs Dick Ellsworth | Seventh | 31½ out |
| Future Cub Mel Hall is born in Lyons, NY. |
| Saturday, September 17 |
| » Defeated Dodgers (77-65), 7-3 | Wrigley Field (30-39) | 54-85 | |
| » Starters: Sandy Koufax vs Don Cardwell | Seventh | 31 out |
| Sunday, September 18 |
| » Defeated Dodgers (77-66), 5-2 | Wrigley Field (31-39) | 55-85 | Won 2 |
| » Starters: Johnny Podres vs Bob Anderson | Seventh | 31½ out |
| Monday, September 19 |
| » Lost to Giants (72-73), 11-4 | Wrigley Field (31-40) | 55-86 | |
| » Starters: Eddie Fisher vs Glen Hobbie | Seventh | 32½ out |
| » Lost to Giants (73-73), 4-1 | Wrigley Field (31-41) | 55-87 | Lost 2 |
| » Starters: Billy O'Dell vs Seth Morehead | Seventh | 32½ out |
| Future Cub Phil Stephenson is born in Guthrie, OK. |
| Tuesday, September 20 |
| » Lost to Giants (74-73), 5-2 | Wrigley Field (31-42) | 55-88 | Lost 3 |
| » Starters: Sam Jones vs Dick Ellsworth | Seventh | 34 out |
| Future Cub Randy Kramer is born in Palo Alto, CA. |
| Thursday, September 22 |
| » Lost to Pirates (91-55), 3-2 | Forbes Field (2-8) | 55-89 | Lost 4 |
| » Starters: Don Cardwell vs Vern Law | Seventh | 36 out |
| » Lost to Pirates (92-55), 6-1 | Forbes Field (2-9) | 55-90 | Lost 5 |
| » Starters: Bob Anderson vs Vinegar Bend Mizell | Seventh | 36 out |
| » Major-league debuts: Dick Bertell (Cubs) |
| Friday, September 23 |
| » Lost to Cardinals (84-61), 5-1 | Wrigley Field (31-43) | 55-91 | Lost 6 |
| » Starters: Ernie Broglio vs Glen Hobbie | Seventh | 36½ out |
| » Lost to Cardinals (85-61), 5-1 | Wrigley Field (31-44) | 55-92 | Lost 7 |
| » Starters: Ray Sadecki vs Seth Morehead | Seventh | 36½ out |
| Saturday, September 24 |
| » Defeated Cardinals (85-62), 5-4 | Wrigley Field (32-44) | 56-92 | |
| » Starters: Bob Miller vs Dick Ellsworth | Seventh | 35½ out |
| Sunday, September 25 |
| » Defeated Cardinals (85-63), 5-0 | Wrigley Field (33-44) | 57-92 | Won 2 |
| » Starters: Larry Jackson vs Glen Hobbie | Seventh | 34½ out |
| Monday, September 26 |
| » Major-league debuts: Matty Alou (Giants) |
| Tuesday, September 27 |
| » Defeated Giants (76-74), 3-1 | Candlestick Park (5-5) | 58-92 | Won 3 |
| » Starters: Don Cardwell vs Billy O'Dell | Seventh | 34½ out |
| Wednesday, September 28 |
| » Defeated Giants (76-75), 6-3 | Candlestick Park (6-5) | 59-92 | Won 4 |
| » Starters: Bob Anderson vs Jack Sanford | Seventh | 34 out |
| Friday, September 30 |
| » Lost to Dodgers (81-71), 7-5 | Los Angeles Memorial Coliseum (4-5) | 59-93 | |
| » Starters: Glen Hobbie vs Jim Golden | Seventh | 34 out |
| » Major-league debuts: Jim Golden (Dodgers) |
| Saturday, October 1 |
| » Defeated Dodgers (81-72), 10-8 | Los Angeles Memorial Coliseum (5-5) | 60-93 | |
| » Starters: Dick Ellsworth vs Phil Ortega | Seventh | 34 out |
| Sunday, October 2 |
| » Lost to Dodgers (82-72), 4-3 | Los Angeles Memorial Coliseum (5-6) | 60-94 | |
| » Starters: Dick Drott vs Ed Rakow | Seventh | 35 out |
