| Saturday, January 5 |
| Future Cub Bob Dernier is born in Kansas City, MO. |
| Tuesday, January 22 |
| Future Cub Brian Dayett is born in New London, CT. |
| Thursday, March 14 |
| Future Cub Steve Lake is born in Inglewood, CA. |
| Monday, April 15 |
| » Major-league debuts: Neil Chrisley (Senators) |
| Tuesday, April 16 |
| » Lost to Braves (1-0), 4-1 | Wrigley Field (0-1) | 0-1 | |
| » Starters: Warren Spahn vs Bob Rush | Second | 1 out |
| » Major-league debuts: Dick Drott, Cal Neeman and Bob Will (Cubs) |
| Thursday, April 18 |
| » Defeated Cardinals (1-1), 10-2 | Sportsman's Park III (1-0) | 1-1 | |
| » Starters: Moe Drabowsky vs Murry Dickson | Second | 1 out |
| » Major-league debuts: Eddie Kasko (Cardinals) |
| Saturday, April 20 |
| » Major-league debuts: Tony Kubek (Yankees) |
| Sunday, April 21 |
| » Defeated Cardinals (1-2), 5-3 | Sportsman's Park III (2-0) | 2-1 | Won 2 |
| » Starters: Don Kaiser vs Herm Wehmeier | Third | 2 out |
| » Lost to Cardinals (2-2), 6-3 | Sportsman's Park III (2-1) | 2-2 | |
| » Starters: Dick Drott vs Sam Jones | Third | 2 out |
| » Major-league debuts: Tom Cheney (Cardinals) |
| Monday, April 22 |
| » Lost to Braves (5-0), 9-4 | County Stadium (0-1) | 2-3 | Lost 2 |
| » Starters: Bob Rush vs Bob Buhl | Fourth | 3 out |
| Tuesday, April 23 |
| » Defeated Braves (5-1), 3-2 | County Stadium (1-1) | 3-3 | |
| » Starters: Elmer Singleton vs Lew Burdette | Third | 2 out |
| Wednesday, April 24 |
| » Lost to Reds (3-4), 9-5 | Crosley Field (0-1) | 3-4 | |
| » Starters: Moe Drabowsky vs Joe Nuxhall | Third | 3 out |
| Thursday, April 25 |
| » Lost to Reds (4-4), 6-3 | Crosley Field (0-2) | 3-5 | Lost 2 |
| » Starters: Dick Drott vs Brooks Lawrence | Fourth | 3½ out |
| Sunday, April 28 |
| » Lost to Cardinals (3-5), 6-2 | Wrigley Field (0-2) | 3-6 | Lost 3 |
| » Starters: Lindy McDaniel vs Bob Rush | Seventh | 6 out |
| » Lost to Cardinals (4-5), 4-0 | Wrigley Field (0-3) | 3-7 | Lost 4 |
| » Starters: Tom Cheney vs Tom Poholsky | Seventh | 6 out |
| Tuesday, April 30 |
| » Lost to Dodgers (8-3), 10-9 | Ebbets Field (0-1) | 3-8 | Lost 5 |
| » Starters: Moe Drabowsky vs Sal Maglie | Seventh | 6 out |
| Wednesday, May 1 |
| » Lost to Dodgers (9-3), 7-2 | Ebbets Field (0-2) | 3-9 | Lost 6 |
| » Starters: Don Kaiser vs Don Drysdale | Eighth | 7 out |
| Thursday, May 2 |
| » Lost to Phillies (6-8), 4-2 | Shibe Park (0-1) | 3-10 | Lost 7 |
| » Starters: Dick Drott vs Robin Roberts | Eighth | 8 out |
| Friday, May 3 |
| » Lost to Phillies (7-8), 9-6 | Shibe Park (0-2) | 3-11 | Lost 8 |
| » Starters: Tom Poholsky vs Don Cardwell | Eighth | 9 out |
| Saturday, May 4 |
| » Lost to Phillies (8-8), 5-2 | Shibe Park (0-3) | 3-12 | Lost 9 |
| » Starters: Jim Brosnan vs Jack Sanford | Eighth | 9 out |
| Sunday, May 5 |
| » Defeated Giants (7-11), 8-3 | Polo Grounds V (1-0) | 4-12 | |
| » Starters: Bob Rush vs Curt Barclay | Eighth | 9½ out |
| » Lost to Giants (8-11), 6-2 | Polo Grounds V (1-1) | 4-13 | |
| » Starters: Moe Drabowsky vs Joe Margoneri | Eighth | 9½ out |
| Monday, May 6 |
| » Defeated Giants (8-12), 6-2 | Polo Grounds V (2-1) | 5-13 | |
| » Starters: Don Kaiser vs Ruben Gomez | Seventh | 8½ out |
| Tuesday, May 7 |
| » Defeated Pirates (5-14), 10-8 | Forbes Field (1-0) | 6-13 | Won 2 |
| » Starters: Tom Poholsky vs Bob Friend | Seventh | 7½ out |
| Wednesday, May 8 |
| » Defeated Pirates (5-15), 7-1 | Forbes Field (2-0) | 7-13 | Won 3 |
| » Starters: Dick Drott vs Vern Law | Seventh | 6½ out |
| Saturday, May 11 |
| » Lost to Reds (14-7), 5-4 | Wrigley Field (0-4) | 7-14 | |
| » Starters: Brooks Lawrence vs Bob Rush | Sixth | 7 out |
| Sunday, May 12 |
| » Lost to Reds (15-7), 7-5 | Wrigley Field (0-5) | 7-15 | Lost 2 |
| » Starters: Hal Jeffcoat vs Don Kaiser | Sixth | 9 out |
| » Lost to Reds (16-7), 7-1 | Wrigley Field (0-6) | 7-16 | Lost 3 |
| » Starters: Don Gross vs Tom Poholsky | Sixth | 9 out |
| Tuesday, May 14 |
| » Lost to Pirates (7-18), 8-6 | Wrigley Field (0-7) | 7-17 | Lost 4 |
| » Starters: Ron Kline vs Dick Drott | Seventh | 10 out |
| Thursday, May 16 |
| » Lost to Dodgers (15-10), 3-2 | Wrigley Field (0-8) | 7-18 | Lost 5 |
| » Starters: Sandy Koufax vs Moe Drabowsky | Eighth | 10½ out |
| Tuesday, May 21 |
| » Defeated Giants (14-18), 4-3 | Wrigley Field (1-8) | 8-18 | |
| » Starters: Stu Miller vs Dick Drott | Sixth | 10½ out |
| Wednesday, May 22 |
| » Lost to Giants (15-18), 4-3 | Wrigley Field (1-9) | 8-19 | |
| » Starters: Ruben Gomez vs Bob Rush | Seventh | 11½ out |
| Friday, May 24 |
| » Defeated Braves (19-11), 5-1 | Wrigley Field (2-9) | 9-19 | |
| » Starters: Warren Spahn vs Moe Drabowsky | Sixth | 11 out |
| » Major-league debuts: Frank Ernaga (Cubs) |
| Saturday, May 25 |
| » Lost to Braves (20-11), 7-6 | Wrigley Field (2-10) | 9-20 | |
| » Starters: Bob Buhl vs Don Kaiser | Seventh | 11 out |
| Sunday, May 26 |
| » Defeated Braves (20-12), 7-5 | Wrigley Field (3-10) | 10-20 | |
| » Starters: Gene Conley vs Dick Drott | Seventh | 10½ out |
| » Defeated Braves (20-13), 5-4 | Wrigley Field (4-10) | 11-20 | Won 2 |
| » Starters: Juan Pizarro vs Elmer Singleton | Seventh | 10½ out |
| Monday, May 27 |
| » Lost to Cardinals (16-18), 6-2 | Sportsman's Park III (2-2) | 11-21 | |
| » Starters: Bob Rush vs Lindy McDaniel | Seventh | 11½ out |
| Tuesday, May 28 |
| » Lost to Cardinals (17-18), 5-1 | Sportsman's Park III (2-3) | 11-22 | Lost 2 |
| » Starters: Moe Drabowsky vs Larry Jackson | Seventh | 11½ out |
| Wednesday, May 29 |
| » Lost to Braves (22-14), 6-2 | County Stadium (1-2) | 11-23 | Lost 3 |
| » Starters: Don Kaiser vs Bob Buhl | Seventh | 12 out |
| Thursday, May 30 |
| » Lost to Braves (23-14), 5-2 | County Stadium (1-3) | 11-24 | Lost 4 |
| » Starters: Dick Drott vs Ray Crone | Seventh | 12 out |
| » Defeated Braves (23-15), 4-2 | County Stadium (2-3) | 12-24 | |
| » Starters: Tom Poholsky vs Taylor Phillips | Seventh | 12 out |
| Saturday, June 1 |
| » Lost to Reds (27-14), 22-2 | Crosley Field (0-3) | 12-25 | |
| » Starters: Dick Littlefield vs Hal Jeffcoat | Seventh | 13 out |
| Sunday, June 2 |
| » Lost to Reds (28-14), 6-4 | Crosley Field (0-4) | 12-26 | Lost 2 |
| » Starters: Moe Drabowsky vs Don Gross | Seventh | 13 out |
| » Defeated Reds (28-15), 4-2 | Crosley Field (1-4) | 13-26 | |
| » Starters: Bob Rush vs Johnny Klippstein | Seventh | 13 out |
| Tuesday, June 4 |
| » Lost to Dodgers (25-17), 7-5 | Ebbets Field (0-3) | 13-27 | |
| » Starters: Dick Drott vs Sandy Koufax | Eighth | 13 out |
| Wednesday, June 5 |
| » Lost to Dodgers (26-17), 4-0 | Roosevelt Stadium (0-1) | 13-28 | Lost 2 |
| » Starters: Don Kaiser vs Don Drysdale | Eighth | 14 out |
| Friday, June 7 |
| » Lost to Phillies (28-19), 1-0 | Shibe Park (0-4) | 13-29 | Lost 3 |
| » Starters: Dave Hillman vs Jack Sanford | Eighth | 13½ out |
| Sunday, June 9 |
| » Defeated Phillies (28-20), 7-3 | Shibe Park (1-4) | 14-29 | |
| » Starters: Dick Drott vs Don Cardwell | Eighth | 13½ out |
| » Tied Phillies, 4-4 | Shibe Park (1-4) | 14-29 | |
| » Starters: Moe Drabowsky vs Harvey Haddix | Eighth | 13½ out |
| Tuesday, June 11 |
| » Lost to Giants (22-31), 5-1 | Polo Grounds V (2-2) | 14-30 | |
| » Starters: Don Kaiser vs Ruben Gomez | Seventh | 13 out |
| Former Cub Fred Raymer dies in Los Angeles, CA at the age of 82. |
| Wednesday, June 12 |
| » Lost to Giants (23-31), 4-3 | Polo Grounds V (2-3) | 14-31 | Lost 2 |
| » Starters: Bob Rush vs Curt Barclay | Seventh | 13 out |
| Thursday, June 13 |
| » Lost to Giants (24-31), 7-4 | Polo Grounds V (2-4) | 14-32 | Lost 3 |
| » Starters: Dave Hillman vs Pete Burnside | Seventh | 13½ out |
| Friday, June 14 |
| » Defeated Pirates (20-33), 11-5 | Forbes Field (3-0) | 15-32 | |
| » Starters: Dick Drott vs Ron Kline | Eighth | 13½ out |
| Saturday, June 15 |
| » Defeated Pirates (20-34), 5-1 | Forbes Field (4-0) | 16-32 | Won 2 |
| » Starters: Moe Drabowsky vs Vern Law | Eighth | 13½ out |
| Sunday, June 16 |
| » Defeated Pirates (20-35), 4-1 | Forbes Field (5-0) | 17-32 | Won 3 |
| » Starters: Don Kaiser vs Luis Arroyo | Seventh | 13½ out |
| » Lost to Pirates (21-35), 5-4 | Forbes Field (5-1) | 17-33 | |
| » Starters: Bob Rush vs Bob Purkey | Seventh | 13½ out |
| Tuesday, June 18 |
| » Lost to Phillies (31-25), 7-6 | Wrigley Field (4-11) | 17-34 | Lost 2 |
| » Starters: Jack Sanford vs Dave Hillman | Eighth | 13 out |
| Former Cub Milo Allison dies in Kenosha, WI at the age of 67. |
| Wednesday, June 19 |
| » Defeated Phillies (31-26), 9-0 | Wrigley Field (5-11) | 18-34 | |
| » Starters: Don Cardwell vs Dick Drott | Eighth | 12½ out |
| » Defeated Phillies (31-27), 4-3 | Wrigley Field (6-11) | 19-34 | Won 2 |
| » Starters: Robin Roberts vs Moe Drabowsky | Eighth | 12½ out |
| Thursday, June 20 |
| » Lost to Phillies (32-27), 7-2 | Wrigley Field (6-12) | 19-35 | |
| » Starters: Harvey Haddix vs Don Kaiser | Seventh | 13 out |
| Friday, June 21 |
| » Lost to Giants (29-33), 12-10 | Wrigley Field (6-13) | 19-36 | Lost 2 |
| » Starters: Ray Crone vs Bob Rush | Eighth | 14 out |
| Saturday, June 22 |
| » Defeated Giants (29-34), 12-4 | Wrigley Field (7-13) | 20-36 | |
| » Starters: Ruben Gomez vs Tom Poholsky | Seventh | 13 out |
| Sunday, June 23 |
| » Lost to Giants (30-34), 7-5 | Wrigley Field (7-14) | 20-37 | |
| » Starters: Johnny Antonelli vs Dick Drott | Eighth | 14½ out |
| » Lost to Giants (31-34), 5-1 | Wrigley Field (7-15) | 20-38 | Lost 2 |
| » Starters: Curt Barclay vs Moe Drabowsky | Eighth | 14½ out |
| Monday, June 24 |
| Future Cub Doug Jones is born in Lebanon, IN. |
| Tuesday, June 25 |
| » Defeated Pirates (24-42), 5-3 | Wrigley Field (8-15) | 21-38 | |
| » Starters: Bob Friend vs Don Kaiser | Seventh | 13½ out |
| Wednesday, June 26 |
| » Lost to Pirates (25-42), 15-5 | Wrigley Field (8-16) | 21-39 | |
| » Starters: Vern Law vs Tom Poholsky | Eighth | 13½ out |
| » Tied Pirates, 5-5 | Wrigley Field (8-16) | 21-39 | |
| » Starters: Joe Trimble vs Moe Drabowsky | Eighth | 13½ out |
| Future Cub Mike Griffin is born in Colusa, CA. |
| Thursday, June 27 |
| » Lost to Pirates (26-42), 5-4 | Wrigley Field (8-17) | 21-40 | Lost 2 |
| » Starters: Bob Purkey vs Dick Drott | Eighth | 14½ out |
| Saturday, June 29 |
| » Lost to Dodgers (36-31), 2-1 | Wrigley Field (8-18) | 21-41 | Lost 3 |
| » Starters: Carl Erskine vs Bob Rush | Eighth | 15½ out |
| Sunday, June 30 |
| » Defeated Dodgers (36-32), 3-2 | Wrigley Field (9-18) | 22-41 | |
| » Starters: Don Newcombe vs Don Elston | Eighth | 16½ out |
| » Lost to Dodgers (37-32), 5-1 | Wrigley Field (9-19) | 22-42 | |
| » Starters: Danny McDevitt vs Moe Drabowsky | Eighth | 16½ out |
| Monday, July 1 |
| » Defeated Reds (42-31), 6-0 | Wrigley Field (10-19) | 23-42 | |
| » Starters: Joe Nuxhall vs Dick Drott | Eighth | 15½ out |
| Tuesday, July 2 |
| » Lost to Reds (43-31), 8-6 | Wrigley Field (10-20) | 23-43 | |
| » Starters: Don Gross vs Don Kaiser | Eighth | 16 out |
| Wednesday, July 3 |
| » Lost to Cardinals (41-30), 5-4 | Wrigley Field (10-21) | 23-44 | Lost 2 |
| » Starters: Larry Jackson vs Tom Poholsky | Eighth | 17 out |
| Thursday, July 4 |
| » Defeated Cardinals (41-31), 7-6 | Wrigley Field (11-21) | 24-44 | |
| » Starters: Lindy McDaniel vs Bob Rush | Eighth | 16½ out |
| » Lost to Cardinals (42-31), 4-3 | Wrigley Field (11-22) | 24-45 | |
| » Starters: Sam Jones vs Moe Drabowsky | Eighth | 16½ out |
| Friday, July 5 |
| » Defeated Braves (43-33), 7-4 | County Stadium (3-3) | 25-45 | |
| » Starters: Don Elston vs Bob Buhl | Seventh | 16 out |
| Saturday, July 6 |
| » Defeated Braves (43-34), 3-2 | County Stadium (4-3) | 26-45 | Won 2 |
| » Starters: Dick Drott vs Warren Spahn | Seventh | 16 out |
| Sunday, July 7 |
| » Lost to Braves (44-34), 4-2 | County Stadium (4-4) | 26-46 | |
| » Starters: Dave Hillman vs Lew Burdette | Eighth | 17½ out |
| Thursday, July 11 |
| » Lost to Phillies (43-35), 1-0 | Shibe Park (1-5) | 26-47 | Lost 2 |
| » Starters: Bob Rush vs Harvey Haddix | Eighth | 18 out |
| » Lost to Phillies (44-35), 3-1 | Shibe Park (1-6) | 26-48 | Lost 3 |
| » Starters: Don Elston vs Jack Sanford | Eighth | 18 out |
| Friday, July 12 |
| » Defeated Phillies (44-36), 5-2 | Shibe Park (2-6) | 27-48 | |
| » Starters: Moe Drabowsky vs Robin Roberts | Eighth | 18 out |
| Saturday, July 13 |
| » Lost to Phillies (45-36), 5-2 | Shibe Park (2-7) | 27-49 | |
| » Starters: Dick Drott vs Warren Hacker | Eighth | 18½ out |
| Sunday, July 14 |
| » Lost to Giants (39-44), 8-6 | Polo Grounds V (2-5) | 27-50 | Lost 2 |
| » Starters: Dave Hillman vs Ray Crone | Seventh | 18 out |
| Monday, July 15 |
| » Lost to Giants (40-44), 5-3 | Polo Grounds V (2-6) | 27-51 | Lost 3 |
| » Starters: Don Elston vs Johnny Antonelli | Eighth | 18 out |
| Tuesday, July 16 |
| » Lost to Pirates (32-54), 5-3 | Forbes Field (5-2) | 27-52 | Lost 4 |
| » Starters: Bob Rush vs Bob Friend | Seventh | 18 out |
| Wednesday, July 17 |
| » Defeated Pirates (32-55), 4-3 | Forbes Field (6-2) | 28-52 | |
| » Starters: Moe Drabowsky vs Ron Kline | Eighth | 18 out |
| Thursday, July 18 |
| » Lost to Pirates (33-55), 6-5 | Forbes Field (6-3) | 28-53 | |
| » Starters: Dick Drott vs Bob Purkey | Seventh | 19 out |
| Friday, July 19 |
| » Lost to Dodgers (48-37), 6-3 | Ebbets Field (0-4) | 28-54 | Lost 2 |
| » Starters: Don Elston vs Sandy Koufax | Eighth | 20½ out |
| » Lost to Dodgers (49-37), 5-3 | Ebbets Field (0-5) | 28-55 | Lost 3 |
| » Starters: Tom Poholsky vs Sal Maglie | Eighth | 20½ out |
| Saturday, July 20 |
| » Lost to Dodgers (50-37), 7-5 | Ebbets Field (0-6) | 28-56 | Lost 4 |
| » Starters: Dave Hillman vs Don Drysdale | Seventh | 21½ out |
| Sunday, July 21 |
| » Defeated Dodgers (50-38), 5-4 | Ebbets Field (1-6) | 29-56 | |
| » Starters: Moe Drabowsky vs Carl Erskine | Seventh | 21½ out |
| » Lost to Dodgers (51-38), 7-2 | Ebbets Field (1-7) | 29-57 | |
| » Starters: Bob Rush vs Don Newcombe | Seventh | 21½ out |
| Tuesday, July 23 |
| » Defeated Giants (42-50), 4-0 | Wrigley Field (12-22) | 30-57 | |
| » Starters: Ramon Monzant vs Dick Drott | Eighth | 21½ out |
| Wednesday, July 24 |
| » Defeated Giants (42-51), 2-1 | Wrigley Field (13-22) | 31-57 | Won 2 |
| » Starters: Johnny Antonelli vs Don Elston | Seventh | 20½ out |
| Thursday, July 25 |
| » Lost to Giants (43-51), 5-2 | Wrigley Field (13-23) | 31-58 | |
| » Starters: Mike McCormick vs Moe Drabowsky | Eighth | 20½ out |
| Friday, July 26 |
| » Lost to Phillies (52-43), 3-1 | Wrigley Field (13-24) | 31-59 | Lost 2 |
| » Starters: Warren Hacker vs Bob Rush | Eighth | 21½ out |
| Saturday, July 27 |
| » Defeated Phillies (52-44), 6-1 | Wrigley Field (14-24) | 32-59 | |
| » Starters: Harvey Haddix vs Jim Brosnan | Eighth | 21½ out |
| Sunday, July 28 |
| » Lost to Phillies (53-44), 3-2 | Wrigley Field (14-25) | 32-60 | |
| » Starters: Curt Simmons vs Tom Poholsky | Eighth | 22½ out |
| » Lost to Phillies (54-44), 7-1 | Wrigley Field (14-26) | 32-61 | Lost 2 |
| » Starters: Jack Sanford vs Dick Drott | Eighth | 22½ out |
| Monday, July 29 |
| » Lost to Phillies (55-44), 6-0 | Wrigley Field (14-27) | 32-62 | Lost 3 |
| » Starters: Robin Roberts vs Don Elston | Eighth | 23½ out |
| Former Cub Tommy Thevenow dies in Madison, IN at the age of 54. |
| Tuesday, July 30 |
| » Lost to Dodgers (55-41), 1-0 | Wrigley Field (14-28) | 32-63 | Lost 4 |
| » Starters: Sal Maglie vs Moe Drabowsky | Eighth | 24 out |
| » Defeated Dodgers (55-42), 4-3 | Wrigley Field (15-28) | 33-63 | |
| » Starters: Don Newcombe vs Dave Hillman | Eighth | 24 out |
| Future Cub Steve Trout is born in Detroit, MI. |
| Wednesday, July 31 |
| » Lost to Dodgers (56-42), 3-2 | Wrigley Field (15-29) | 33-64 | |
| » Starters: Don Drysdale vs Bob Rush | Eighth | 25½ out |
| » Lost to Dodgers (57-42), 2-1 | Wrigley Field (15-30) | 33-65 | Lost 2 |
| » Starters: Roger Craig vs Jim Brosnan | Eighth | 25½ out |
| » Major-league debuts: Bob Anderson (Cubs) |
| Future Cub Leon Durham is born in Cincinnati, OH. |
| Thursday, August 1 |
| » Lost to Dodgers (58-42), 12-3 | Wrigley Field (15-31) | 33-66 | Lost 3 |
| » Starters: Sandy Koufax vs Tom Poholsky | Eighth | 26½ out |
| Friday, August 2 |
| » Defeated Pirates (36-67), 6-4 | Wrigley Field (16-31) | 34-66 | |
| » Starters: Vern Law vs Dick Drott | Eighth | 26½ out |
| Sunday, August 4 |
| » Defeated Pirates (36-68), 6-0 | Wrigley Field (17-31) | 35-66 | Won 2 |
| » Starters: Bob Friend vs Moe Drabowsky | Seventh | 26 out |
| » Defeated Pirates (36-69), 3-2 | Wrigley Field (18-31) | 36-66 | Won 3 |
| » Starters: Bob Purkey vs Don Elston | Seventh | 26 out |
| Tuesday, August 6 |
| » Defeated Cardinals (63-42), 8-2 | Sportsman's Park III (3-3) | 37-66 | Won 4 |
| » Starters: Bob Rush vs Sam Jones | Sixth | 25 out |
| Wednesday, August 7 |
| » Defeated Cardinals (63-43), 5-1 | Sportsman's Park III (4-3) | 38-66 | Won 5 |
| » Starters: Dick Drott vs Herm Wehmeier | Seventh | 25 out |
| Thursday, August 8 |
| » Defeated Cardinals (63-44), 4-3 | Sportsman's Park III (5-3) | 39-66 | Won 6 |
| » Starters: Moe Drabowsky vs Vinegar Bend Mizell | Seventh | 25 out |
| Future Cub Ray Fontenot is born in Lake Charles, LA. |
| Friday, August 9 |
| » Lost to Reds (59-49), 9-7 | Crosley Field (1-5) | 39-67 | |
| » Starters: Jim Brosnan vs Vicente Amor | Seventh | 26½ out |
| » Lost to Reds (60-49), 6-4 | Crosley Field (1-6) | 39-68 | Lost 2 |
| » Starters: Don Elston vs Art Fowler | Seventh | 26½ out |
| Saturday, August 10 |
| » Lost to Reds (61-49), 7-2 | Crosley Field (1-7) | 39-69 | Lost 3 |
| » Starters: Dave Hillman vs Hal Jeffcoat | Seventh | 27½ out |
| Tuesday, August 13 |
| » Defeated Cardinals (63-48), 6-2 | Wrigley Field (19-31) | 40-69 | |
| » Starters: Herm Wehmeier vs Bob Rush | Seventh | 28 out |
| Wednesday, August 14 |
| » Defeated Cardinals (63-49), 3-1 | Wrigley Field (20-31) | 41-69 | Won 2 |
| » Starters: Vinegar Bend Mizell vs Dick Drott | Seventh | 28 out |
| Thursday, August 15 |
| » Defeated Cardinals (63-50), 4-1 | Wrigley Field (21-31) | 42-69 | Won 3 |
| » Starters: Sam Jones vs Moe Drabowsky | Seventh | 28 out |
| Friday, August 16 |
| » Defeated Reds (61-53), 8-6 | Wrigley Field (22-31) | 43-69 | Won 4 |
| » Starters: Art Fowler vs Don Elston | Seventh | 27 out |
| Saturday, August 17 |
| » Defeated Reds (61-54), 2-1 | Wrigley Field (23-31) | 44-69 | Won 5 |
| » Starters: Hal Jeffcoat vs Dave Hillman | Seventh | 27 out |
| Future Cub Bill Landrum is born in Columbia, SC. |
| Sunday, August 18 |
| » Defeated Reds (61-55), 8-2 | Wrigley Field (24-31) | 45-69 | Won 6 |
| » Starters: Joe Nuxhall vs Bob Rush | Seventh | 25½ out |
| Tuesday, August 20 |
| » Lost to Phillies (61-57), 2-1 | Shibe Park (2-8) | 45-70 | |
| » Starters: Moe Drabowsky vs Curt Simmons | Seventh | 26 out |
| » Defeated Phillies (61-58), 5-2 | Shibe Park (3-8) | 46-70 | |
| » Starters: Jim Brosnan vs Robin Roberts | Seventh | 26 out |
| Thursday, August 22 |
| » Lost to Giants (58-66), 6-2 | Polo Grounds V (2-7) | 46-71 | |
| » Starters: Dick Drott vs Ray Crone | Sixth | 27 out |
| Friday, August 23 |
| » Lost to Giants (59-66), 3-2 | Polo Grounds V (2-8) | 46-72 | Lost 2 |
| » Starters: Bob Rush vs Al Worthington | Sixth | 27 out |
| Saturday, August 24 |
| » Defeated Giants (59-67), 4-2 | Polo Grounds V (3-8) | 47-72 | |
| » Starters: Dave Hillman vs Johnny Antonelli | Sixth | 27 out |
| Sunday, August 25 |
| » Lost to Pirates (46-76), 3-0 | Forbes Field (6-4) | 47-73 | |
| » Starters: Moe Drabowsky vs Vern Law | Sixth | 27½ out |
| » Defeated Pirates (46-77), 8-2 | Forbes Field (7-4) | 48-73 | |
| » Starters: Don Elston vs Whammy Douglas | Sixth | 27½ out |
| Tuesday, August 27 |
| » Defeated Dodgers (70-56), 9-4 | Ebbets Field (2-7) | 49-73 | Won 2 |
| » Starters: Dick Drott vs Don Newcombe | Sixth | 27 out |
| Wednesday, August 28 |
| » Lost to Dodgers (71-56), 4-3 | Ebbets Field (2-8) | 49-74 | |
| » Starters: Bob Rush vs Sandy Koufax | Seventh | 27 out |
| Friday, August 30 |
| » Lost to Cardinals (71-56), 2-1 | Wrigley Field (24-32) | 49-75 | Lost 2 |
| » Starters: Vinegar Bend Mizell vs Moe Drabowsky | Sixth | 28 out |
| Saturday, August 31 |
| » Lost to Cardinals (72-56), 3-2 | Wrigley Field (24-33) | 49-76 | Lost 3 |
| » Starters: Herm Wehmeier vs Don Elston | Seventh | 29 out |
| Sunday, September 1 |
| » Lost to Cardinals (73-56), 3-2 | Wrigley Field (24-34) | 49-77 | Lost 4 |
| » Starters: Sam Jones vs Dick Drott | Seventh | 29 out |
| Monday, September 2 |
| » Lost to Braves (80-49), 23-10 | Wrigley Field (24-35) | 49-78 | Lost 5 |
| » Starters: Lew Burdette vs Bob Rush | Seventh | 31 out |
| » Lost to Braves (81-49), 4-0 | Wrigley Field (24-36) | 49-79 | Lost 6 |
| » Starters: Bob Trowbridge vs Dave Hillman | Seventh | 31 out |
| Tuesday, September 3 |
| » Lost to Braves (82-49), 8-0 | Wrigley Field (24-37) | 49-80 | Lost 7 |
| » Starters: Warren Spahn vs Dick Littlefield | Seventh | 32 out |
| Wednesday, September 4 |
| » Defeated Reds (67-66), 1-0 | Wrigley Field (25-37) | 50-80 | |
| » Starters: Bud Podbielan vs Moe Drabowsky | Seventh | 31½ out |
| » Lost to Reds (68-66), 7-2 | Wrigley Field (25-38) | 50-81 | |
| » Starters: Joe Nuxhall vs Don Elston | Seventh | 31½ out |
| Thursday, September 5 |
| » Lost to Reds (69-66), 4-1 | Wrigley Field (25-39) | 50-82 | Lost 2 |
| » Starters: Brooks Lawrence vs Dick Drott | Seventh | 31½ out |
| Friday, September 6 |
| » Defeated Braves (82-52), 5-4 | County Stadium (5-4) | 51-82 | |
| » Starters: Bob Rush vs Bob Trowbridge | Eighth | 30½ out |
| Saturday, September 7 |
| » Lost to Braves (83-52), 7-2 | County Stadium (5-5) | 51-83 | |
| » Starters: Dave Hillman vs Warren Spahn | Eighth | 31½ out |
| Sunday, September 8 |
| » Defeated Braves (83-53), 5-3 | County Stadium (6-5) | 52-83 | |
| » Starters: Moe Drabowsky vs Gene Conley | Eighth | 30½ out |
| » Major-league debuts: Eddie Haas (Cubs) |
| Tuesday, September 10 |
| » Defeated Dodgers (77-62), 9-2 | Wrigley Field (26-39) | 53-83 | Won 2 |
| » Starters: Sandy Koufax vs Dick Drott | Seventh | 30½ out |
| » Major-league debuts: Jim Gentile and Fred Kipp (Dodgers) |
| Wednesday, September 11 |
| » Lost to Dodgers (78-62), 9-1 | Wrigley Field (26-40) | 53-84 | |
| » Starters: Johnny Podres vs Bob Rush | Eighth | 30½ out |
| Friday, September 13 |
| » Lost to Pirates (56-85), 4-1 | Wrigley Field (26-41) | 53-85 | Lost 2 |
| » Starters: Bob Friend vs Don Elston | Eighth | 31½ out |
| » Lost to Pirates (57-85), 2-1 | Wrigley Field (26-42) | 53-86 | Lost 3 |
| » Starters: Bob Smith vs Moe Drabowsky | Eighth | 31½ out |
| Saturday, September 14 |
| » Lost to Pirates (58-85), 3-1 | Wrigley Field (26-43) | 53-87 | Lost 4 |
| » Starters: Eddie O'Brien vs Dick Drott | Eighth | 31 out |
| » Defeated Pirates (58-86), 7-3 | Wrigley Field (27-43) | 54-87 | |
| » Starters: Whammy Douglas vs Dave Hillman | Eighth | 31 out |
| Sunday, September 15 |
| » Defeated Giants (68-77), 6-2 | Wrigley Field (28-43) | 55-87 | Won 2 |
| » Starters: Ray Crone vs Bob Rush | Eighth | 29½ out |
| » Defeated Giants (68-78), 7-6 | Wrigley Field (29-43) | 56-87 | Won 3 |
| » Starters: Mike McCormick vs Ed Mayer | Eighth | 29½ out |
| Tuesday, September 17 |
| » Defeated Phillies (72-74), 7-1 | Wrigley Field (30-43) | 57-87 | Won 4 |
| » Starters: Jack Sanford vs Moe Drabowsky | Seventh | 30 out |
| Wednesday, September 18 |
| » Defeated Phillies (72-75), 6-4 | Wrigley Field (31-43) | 58-87 | Won 5 |
| » Starters: Robin Roberts vs Dick Drott | Seventh | 30 out |
| Friday, September 20 |
| » Lost to Braves (89-57), 9-3 | Wrigley Field (31-44) | 58-88 | |
| » Starters: Warren Spahn vs Bob Rush | Seventh | 31 out |
| » Major-league debuts: Johnny Goryl and Glen Hobbie (Cubs) |
| Saturday, September 21 |
| » Lost to Braves (90-57), 6-2 | Wrigley Field (31-45) | 58-89 | Lost 2 |
| » Starters: Bob Buhl vs Moe Drabowsky | Seventh | 32 out |
| Sunday, September 22 |
| » Lost to Braves (91-57), 9-7 | Wrigley Field (31-46) | 58-90 | Lost 3 |
| » Starters: Bob Trowbridge vs Dick Drott | Eighth | 33 out |
| Monday, September 23 |
| Future Cub Tony Fossas is born in Havana, Cuba. |
| Tuesday, September 24 |
| » Lost to Reds (78-71), 4-3 | Crosley Field (1-8) | 58-91 | Lost 4 |
| » Starters: Don Kaiser vs Hal Jeffcoat | Eighth | 35 out |
| » Lost to Reds (79-71), 11-9 | Crosley Field (1-9) | 58-92 | Lost 5 |
| » Starters: Dave Hillman vs Bud Podbielan | Eighth | 35 out |
| Wednesday, September 25 |
| » Defeated Reds (79-72), 7-5 | Crosley Field (2-9) | 59-92 | |
| » Starters: Moe Drabowsky vs Jay Hook | Eighth | 34 out |
| » Major-league debuts: Dutch Dotterer and Dave Skaugstad (Reds) |
| Friday, September 27 |
| » Defeated Cardinals (87-65), 3-2 | Sportsman's Park III (6-3) | 60-92 | Won 2 |
| » Starters: Dick Drott vs Lynn Lovenguth | Seventh | 34 out |
| Saturday, September 28 |
| » Defeated Cardinals (87-66), 6-4 | Sportsman's Park III (7-3) | 61-92 | Won 3 |
| » Starters: Bob Rush vs Morrie Martin | Seventh | 33 out |
| Sunday, September 29 |
| » Defeated Cardinals (87-67), 8-3 | Sportsman's Park III (8-3) | 62-92 | Won 4 |
| » Starters: Moe Drabowsky vs Frank Barn |
