| Sunday, February 6 |
| Future Cub Smoky Burgess is born in Caroleen, NC. |
| Saturday, March 19 |
| Future Cub Richie Ashburn is born in Tilden, NE. |
| Monday, March 21 |
| Future Cub Owen Friend is born in Granite City, IL. |
| Tuesday, April 12 |
| » Defeated Cardinals (0-1), 10-1 | Wrigley Field (1-0) | 1-0 | |
| » Starters: Pete Alexander vs Charlie Root | First | -- |
| Wednesday, April 13 |
| » Lost to Cardinals (1-1), 5-0 | Wrigley Field (1-1) | 1-1 | |
| » Starters: Jesse Haines vs Sheriff Blake | Second | ½ out |
| Friday, April 15 |
| » Defeated Cardinals (1-2), 1-0 | Wrigley Field (2-1) | 2-1 | |
| » Starters: Bill Sherdel vs Percy Jones | Third | 1 out |
| Saturday, April 16 |
| » Defeated Pirates (3-1), 5-2 | Wrigley Field (3-1) | 3-1 | Won 2 |
| » Starters: Carmen Hill vs Guy Bush | First | -- |
| Sunday, April 17 |
| » Lost to Pirates (4-1), 8-3 | Wrigley Field (3-2) | 3-2 | |
| » Starters: Ray Kremer vs Charlie Root | Fourth | 1 out |
| Monday, April 18 |
| » Lost to Pirates (5-1), 9-1 | Wrigley Field (3-3) | 3-3 | Lost 2 |
| » Starters: Lee Meadows vs Tony Kaufmann | Fifth | 2 out |
| Wednesday, April 20 |
| » Lost to Cardinals (4-3), 4-2 | Sportsman's Park III (0-1) | 3-4 | Lost 3 |
| » Starters: Sheriff Blake vs Bill Sherdel | Fifth | 2½ out |
| Saturday, April 23 |
| » Lost to Cardinals (5-3), 7-0 | Sportsman's Park III (0-2) | 3-5 | Lost 4 |
| » Starters: Percy Jones vs Flint Rhem | Sixth | 3½ out |
| Sunday, April 24 |
| » Defeated Reds (2-8), 5-3 | Crosley Field (1-0) | 4-5 | |
| » Starters: Charlie Root vs Art Nehf | Sixth | 2½ out |
| Monday, April 25 |
| » Lost to Reds (3-8), 11-9 | Crosley Field (1-1) | 4-6 | |
| » Starters: Guy Bush vs Eppa Rixey | Fourth | 3 out |
| Tuesday, April 26 |
| » Lost to Reds (4-8), 8-5 | Crosley Field (1-2) | 4-7 | Lost 2 |
| » Starters: Percy Jones vs Dolf Luque | Fourth | 3½ out |
| » Major-league debuts: Woody English (Cubs) |
| Wednesday, April 27 |
| » Defeated Reds (4-9), 2-1 | Crosley Field (2-2) | 5-7 | |
| » Starters: Sheriff Blake vs Pete Donohue | Fourth | 3 out |
| Thursday, April 28 |
| » Defeated Pirates (8-5), 16-4 | Forbes Field (1-0) | 6-7 | Won 2 |
| » Starters: Charlie Root vs Joe Bush | Fifth | 3 out |
| Saturday, April 30 |
| » Defeated Pirates (8-6), 5-4 | Forbes Field (2-0) | 7-7 | Won 3 |
| » Starters: Bob Osborn vs Vic Aldridge | Fourth | 3½ out |
| Sunday, May 1 |
| » Lost to Pirates (9-6), 7-6 | Wrigley Field (3-4) | 7-8 | |
| » Starters: Ray Kremer vs Guy Bush | Sixth | 3½ out |
| Tuesday, May 3 |
| » Defeated Reds (5-13), 4-3 | Wrigley Field (4-4) | 8-8 | |
| » Starters: Dolf Luque vs Sheriff Blake | Fourth | 2 out |
| Wednesday, May 4 |
| » Defeated Reds (5-14), 13-9 | Wrigley Field (5-4) | 9-8 | Won 2 |
| » Starters: Pete Donohue vs Tony Kaufmann | Fifth | 2 out |
| Saturday, May 7 |
| » Defeated Giants (13-8), 6-4 | Polo Grounds V (1-0) | 10-8 | Won 3 |
| » Starters: Charlie Root vs Freddie Fitzsimmons | Fourth | 1½ out |
| Sunday, May 8 |
| » Lost to Giants (14-8), 5-4 | Polo Grounds V (1-1) | 10-9 | |
| » Starters: Guy Bush vs Virgil Barnes | Fourth | 2½ out |
| Tuesday, May 10 |
| » Defeated Phillies (9-8), 6-3 | Baker Bowl (1-0) | 11-9 | |
| » Starters: Sheriff Blake vs Hal Carlson | Third | 2 out |
| Wednesday, May 11 |
| » Lost to Phillies (10-8), 5-2 | Baker Bowl (1-1) | 11-10 | |
| » Starters: Bob Osborn vs Alex Ferguson | Fifth | 3 out |
| Thursday, May 12 |
| » Defeated Phillies (10-9), 4-1 | Baker Bowl (2-1) | 12-10 | |
| » Starters: Charlie Root vs Jack Scott | Fourth | 3 out |
| Friday, May 13 |
| » Lost to Phillies (11-9), 4-1 | Baker Bowl (2-2) | 12-11 | |
| » Starters: Tony Kaufmann vs Hub Pruett | Fourth | 3 out |
| Saturday, May 14 |
| » Defeated Braves (9-13), 7-2 | Braves Field (1-0) | 13-11 | |
| » Starters: Guy Bush vs Charlie Robertson | Fourth | 3 out |
| Tuesday, May 17 |
| » Defeated Braves (9-14), 4-3 | Braves Field (2-0) | 14-11 | Won 2 |
| » Starters: Sheriff Blake vs Bob Smith | Fourth | 3½ out |
| Wednesday, May 18 |
| » Defeated Dodgers (13-18), 7-4 | Ebbets Field (1-0) | 15-11 | Won 3 |
| » Starters: Charlie Root vs Bill Doak | Second | 2½ out |
| Friday, May 20 |
| » Defeated Dodgers (13-19), 7-5 | Ebbets Field (2-0) | 16-11 | Won 4 |
| » Starters: Tony Kaufmann vs Jumbo Elliott | Second | 1½ out |
| Saturday, May 21 |
| » Defeated Dodgers (13-20), 6-4 | Ebbets Field (3-0) | 17-11 | Won 5 |
| » Starters: Guy Bush vs Jesse Petty | First | -- |
| » Defeated Dodgers (13-21), 11-6 | Ebbets Field (4-0) | 18-11 | Won 6 |
| » Starters: Sheriff Blake vs Doug McWeeny | First | -- |
| Future Cub Elvin Tappe is born in Quincy, IL. |
| Sunday, May 22 |
| » Lost to Reds (11-21), 8-4 | Crosley Field (2-3) | 18-12 | |
| » Starters: Charlie Root vs Red Lucas | Second | 1 out |
| Wednesday, May 25 |
| » Lost to Cardinals (18-12), 8-5 | Wrigley Field (5-5) | 18-13 | Lost 2 |
| » Starters: Pete Alexander vs Tony Kaufmann | Second | 1½ out |
| » Defeated Cardinals (18-13), 8-4 | Wrigley Field (6-5) | 19-13 | |
| » Starters: Bill Sherdel vs Bob Osborn | Second | 1½ out |
| Thursday, May 26 |
| » Defeated Reds (11-25), 11-2 | Wrigley Field (7-5) | 20-13 | Won 2 |
| » Starters: Eppa Rixey vs Charlie Root | Second | 1½ out |
| Friday, May 27 |
| » Defeated Reds (11-26), 3-2 | Wrigley Field (8-5) | 21-13 | Won 3 |
| » Starters: Jakie May vs Guy Bush | Second | 1½ out |
| Saturday, May 28 |
| » Lost to Reds (12-26), 8-0 | Wrigley Field (8-6) | 21-14 | |
| » Starters: Pete Donohue vs Sheriff Blake | Second | 2½ out |
| Sunday, May 29 |
| » Lost to Pirates (24-11), 8-5 | Wrigley Field (8-7) | 21-15 | Lost 2 |
| » Starters: Carmen Hill vs Bob Osborn | Second | 3½ out |
| Monday, May 30 |
| » Defeated Pirates (24-12), 7-6 | Forbes Field (3-0) | 22-15 | |
| » Starters: Tony Kaufmann vs Joe Bush | Second | 3½ out |
| » Lost to Pirates (25-12), 6-5 | Forbes Field (3-1) | 22-16 | |
| » Starters: Charlie Root vs Vic Aldridge | Second | 3½ out |
| Tuesday, May 31 |
| » Lost to Pirates (26-12), 10-9 | Forbes Field (3-2) | 22-17 | Lost 2 |
| » Starters: Jim Brillheart vs Mike Cvengros | Third | 4½ out |
| Friday, June 3 |
| » Lost to Braves (14-21), 5-4 | Wrigley Field (8-8) | 22-18 | Lost 3 |
| » Starters: Charlie Robertson vs Guy Bush | Fourth | 5½ out |
| Saturday, June 4 |
| » Lost to Braves (15-21), 10-8 | Wrigley Field (8-9) | 22-19 | Lost 4 |
| » Starters: Bob Smith vs Charlie Root | Fourth | 6 out |
| Sunday, June 5 |
| » Defeated Braves (15-22), 7-0 | Wrigley Field (9-9) | 23-19 | |
| » Starters: Foster Edwards vs Sheriff Blake | Fourth | 5½ out |
| Monday, June 6 |
| » Defeated Braves (15-23), 4-3 | Wrigley Field (10-9) | 24-19 | Won 2 |
| » Starters: Larry Benton vs Jim Brillheart | Third | 5½ out |
| Future Cub Bob Talbot is born in Visalia, CA. |
| Tuesday, June 7 |
| » Defeated Dodgers (23-27), 7-6 | Wrigley Field (11-9) | 25-19 | Won 3 |
| » Starters: Doug McWeeny vs Charlie Root | Third | 5½ out |
| Wednesday, June 8 |
| » Defeated Dodgers (23-28), 3-2 | Wrigley Field (12-9) | 26-19 | Won 4 |
| » Starters: Dazzy Vance vs Hal Carlson | Second | 4½ out |
| Thursday, June 9 |
| » Defeated Dodgers (23-29), 4-3 | Wrigley Field (13-9) | 27-19 | Won 5 |
| » Starters: Jesse Petty vs Bob Osborn | Second | 3½ out |
| Friday, June 10 |
| » Defeated Dodgers (23-30), 5-4 | Wrigley Field (14-9) | 28-19 | Won 6 |
| » Starters: Doug McWeeny vs Jim Brillheart | Second | 3½ out |
| Saturday, June 11 |
| » Defeated Giants (26-22), 2-1 | Wrigley Field (15-9) | 29-19 | Won 7 |
| » Starters: Burleigh Grimes vs Charlie Root | Second | 2½ out |
| Sunday, June 12 |
| » Defeated Giants (26-23), 7-6 | Wrigley Field (16-9) | 30-19 | Won 8 |
| » Starters: Virgil Barnes vs Hal Carlson | Second | 1½ out |
| Monday, June 13 |
| » Defeated Giants (26-24), 6-2 | Wrigley Field (17-9) | 31-19 | Won 9 |
| » Starters: Freddie Fitzsimmons vs Sheriff Blake | Second | 1½ out |
| Tuesday, June 14 |
| » Defeated Giants (26-25), 4-3 | Wrigley Field (18-9) | 32-19 | Won 10 |
| » Starters: Larry Benton vs Jim Brillheart | Second | 1 out |
| Wednesday, June 15 |
| » Defeated Phillies (19-30), 12-5 | Wrigley Field (19-9) | 33-19 | Won 11 |
| » Starters: Claude Willoughby vs Charlie Root | Second | 1 out |
| Thursday, June 16 |
| » Defeated Phillies (19-31), 7-2 | Wrigley Field (20-9) | 34-19 | Won 12 |
| » Starters: Hub Pruett vs Hal Carlson | Second | 1 out |
| Friday, June 17 |
| » Lost to Phillies (20-31), 12-2 | Wrigley Field (20-10) | 34-20 | |
| » Starters: Clarence Mitchell vs Sheriff Blake | Second | 1 out |
| Saturday, June 18 |
| » Lost to Phillies (21-31), 7-2 | Wrigley Field (20-11) | 34-21 | Lost 2 |
| » Starters: Alex Ferguson vs Bob Osborn | Second | 2 out |
| Sunday, June 19 |
| » Defeated Pirates (35-19), 14-7 | Wrigley Field (21-11) | 35-21 | |
| » Starters: Carmen Hill vs Charlie Root | Second | 1 out |
| Monday, June 20 |
| » Lost to Pirates (36-19), 4-0 | Wrigley Field (21-12) | 35-22 | |
| » Starters: Lee Meadows vs Hal Carlson | Second | 2 out |
| Tuesday, June 21 |
| » Lost to Cardinals (32-22), 6-5 | Sportsman's Park III (0-3) | 35-23 | Lost 2 |
| » Starters: Sheriff Blake vs Jesse Haines | Third | 2½ out |
| » Lost to Cardinals (33-22), 12-3 | Sportsman's Park III (0-4) | 35-24 | Lost 3 |
| » Starters: Jim Brillheart vs Flint Rhem | Third | 2½ out |
| » Major-league debuts: Hank Grampp (Cubs) |
| Future Cub Jackie Collum is born in Victor, IA. |
| Wednesday, June 22 |
| » Lost to Cardinals (34-22), 11-5 | Sportsman's Park III (0-5) | 35-25 | Lost 4 |
| » Starters: Bob Osborn vs Pete Alexander | Third | 3½ out |
| Friday, June 24 |
| » Defeated Pirates (37-21), 4-2 | Forbes Field (4-2) | 36-25 | |
| » Starters: Charlie Root vs Lee Meadows | Third | 2½ out |
| Saturday, June 25 |
| » Defeated Pirates (37-22), 6-4 | Forbes Field (5-2) | 37-25 | Won 2 |
| » Starters: Hal Carlson vs Vic Aldridge | Third | 1½ out |
| Sunday, June 26 |
| » Lost to Reds (24-41), 8-5 | Crosley Field (2-4) | 37-26 | |
| » Starters: Sheriff Blake vs Dolf Luque | Third | 2½ out |
| Monday, June 27 |
| » Defeated Reds (24-42), 11-4 | Crosley Field (3-4) | 38-26 | |
| » Starters: Jim Brillheart vs Jakie May | Third | 1½ out |
| Tuesday, June 28 |
| » Lost to Reds (25-42), 8-1 | Crosley Field (3-5) | 38-27 | |
| » Starters: Charlie Root vs Eppa Rixey | Third | 2½ out |
| Wednesday, June 29 |
| » Defeated Reds (25-43), 2-1 | Crosley Field (4-5) | 39-27 | |
| » Starters: Bob Osborn vs Red Lucas | Third | 1½ out |
| Friday, July 1 |
| » Defeated Cardinals (39-26), 6-2 | Wrigley Field (22-12) | 40-27 | Won 2 |
| » Starters: Flint Rhem vs Hal Carlson | Third | 1½ out |
| Saturday, July 2 |
| » Defeated Cardinals (39-27), 7-4 | Wrigley Field (23-12) | 41-27 | Won 3 |
| » Starters: Jesse Haines vs Sheriff Blake | Second | 1½ out |
| Sunday, July 3 |
| » Defeated Cardinals (39-28), 7-4 | Wrigley Field (24-12) | 42-27 | Won 4 |
| » Starters: Bob McGraw vs Charlie Root | Second | 1½ out |
| Monday, July 4 |
| » Defeated Reds (26-46), 6-3 | Wrigley Field (25-12) | 43-27 | Won 5 |
| » Starters: Pete Donohue vs Bob Osborn | Second | 1½ out |
| » Defeated Reds (26-47), 2-1 | Wrigley Field (26-12) | 44-27 | Won 6 |
| » Starters: Jakie May vs Jim Brillheart | Second | 1½ out |
| Tuesday, July 5 |
| » Defeated Reds (26-48), 8-5 | Wrigley Field (27-12) | 45-27 | Won 7 |
| » Starters: Dolf Luque vs Bob Osborn | Second | 1½ out |
| Thursday, July 7 |
| » Defeated Pirates (44-26), 2-1 | Forbes Field (6-2) | 46-27 | Won 8 |
| » Starters: Hal Carlson vs Joe Dawson | First | -- |
| Friday, July 8 |
| » Defeated Pirates (44-27), 1-0 | Forbes Field (7-2) | 47-27 | Won 9 |
| » Starters: Charlie Root vs Lee Meadows | First | -- |
| Saturday, July 9 |
| » Lost to Pirates (45-27), 4-0 | Forbes Field (7-3) | 47-28 | |
| » Starters: Jim Brillheart vs Vic Aldridge | First | -- |
| Sunday, July 10 |
| » Defeated Dodgers (37-41), 1-0 | Ebbets Field (5-0) | 48-28 | |
| » Starters: Guy Bush vs Norman Plitt | First | -- |
| Tuesday, July 12 |
| » Defeated Braves (29-44), 6-2 | Braves Field (3-0) | 49-28 | Won 2 |
| » Starters: Sheriff Blake vs Joe Genewich | First | -- |
| Wednesday, July 13 |
| » Lost to Braves (30-44), 6-3 | Braves Field (3-1) | 49-29 | |
| » Starters: Hal Carlson vs Kent Greenfield | First | -- |
| » Defeated Braves (30-45), 4-1 | Braves Field (4-1) | 50-29 | |
| » Starters: Charlie Root vs Bob Smith | First | -- |
| Thursday, July 14 |
| » Defeated Braves (30-46), 6-1 | Braves Field (5-1) | 51-29 | Won 2 |
| » Starters: Bob Osborn vs Charlie Robertson | First | -- |
| Friday, July 15 |
| » Defeated Braves (30-47), 9-6 | Braves Field (6-1) | 52-29 | Won 3 |
| » Starters: Jim Brillheart vs Foster Edwards | First | -- |
| Saturday, July 16 |
| » Lost to Giants (45-41), 6-5 | Polo Grounds V (1-2) | 52-30 | |
| » Starters: Guy Bush vs Larry Benton | First | -- |
| » Lost to Giants (46-41), 4-2 | Polo Grounds V (1-3) | 52-31 | Lost 2 |
| » Starters: Sheriff Blake vs Dutch Henry | First | -- |
| Monday, July 18 |
| » Defeated Giants (46-42), 6-4 | Polo Grounds V (2-3) | 53-31 | |
| » Starters: Hal Carlson vs Freddie Fitzsimmons | Second | 2½ out |
| » Lost to Giants (47-42), 3-2 | Polo Grounds V (2-4) | 53-32 | |
| » Starters: Charlie Root vs Virgil Barnes | Second | 2½ out |
| Tuesday, July 19 |
| » Defeated Giants (47-43), 8-5 | Polo Grounds V (3-4) | 54-32 | |
| » Starters: Bob Osborn vs Bill Clarkson | First | -- |
| Wednesday, July 20 |
| » Lost to Giants (48-43), 5-4 | Polo Grounds V (3-5) | 54-33 | |
| » Starters: Jim Brillheart vs Burleigh Grimes | Second | 2½ out |
| Thursday, July 21 |
| » Lost to Phillies (36-51), 7-3 | Baker Bowl (2-3) | 54-34 | Lost 2 |
| » Starters: Guy Bush vs Hub Pruett | First | -- |
| Friday, July 22 |
| » Lost to Phillies (37-51), 6-5 | Baker Bowl (2-4) | 54-35 | Lost 3 |
| » Starters: Charlie Root vs Dutch Ulrich | Second | 2 out |
| Sunday, July 24 |
| » Lost to Dodgers (41-49), 3-2 | Ebbets Field (5-1) | 54-36 | Lost 4 |
| » Starters: Hal Carlson vs Jesse Petty | Second | 1 out |
| » Defeated Dodgers (41-50), 7-1 | Ebbets Field (6-1) | 55-36 | |
| » Starters: Sheriff Blake vs Norman Plitt | Second | 1 out |
| Future Cub Preston Ward is born in Columbia, MO. |
| Wednesday, July 27 |
| » Lost to Giants (51-46), 6-4 | Wrigley Field (27-13) | 55-37 | |
| » Starters: Freddie Fitzsimmons vs Charlie Root | Second | 1 out |
| Thursday, July 28 |
| » Lost to Giants (52-46), 6-5 | Wrigley Field (27-14) | 55-38 | Lost 2 |
| » Starters: Burleigh Grimes vs Guy Bush | Second | 1 out |
| Friday, July 29 |
| » Defeated Giants (52-47), 5-4 | Wrigley Field (28-14) | 56-38 | |
| » Starters: Larry Benton vs Hal Carlson | Second | 1 out |
| Saturday, July 30 |
| » Lost to Phillies (38-54), 5-3 | Wrigley Field (28-15) | 56-39 | |
| » Starters: Dutch Ulrich vs Sheriff Blake | Second | 1 out |
| Sunday, July 31 |
| » Defeated Phillies (38-55), 12-5 | Wrigley Field (29-15) | 57-39 | |
| » Starters: Hub Pruett vs Charlie Root | Second | ½ out |
| Monday, August 1 |
| » Defeated Phillies (38-56), 6-5 | Wrigley Field (30-15) | 58-39 | Won 2 |
| » Starters: Jack Scott vs Jim Brillheart | First | -- |
| Tuesday, August 2 |
| » Defeated Phillies (38-57), 6-2 | Wrigley Field (31-15) | 59-39 | Won 3 |
| » Starters: Alex Ferguson vs Guy Bush | First | -- |
| Wednesday, August 3 |
| » Defeated Braves (38-56), 12-1 | Wrigley Field (32-15) | 60-39 | Won 4 |
| » Starters: Charlie Robertson vs Hal Carlson | First | -- |
| Thursday, August 4 |
| » Defeated Braves (38-57), 5-4 | Wrigley Field (33-15) | 61-39 | Won 5 |
| » Starters: Joe Genewich vs Charlie Root | First | -- |
| Friday, August 5 |
| » Defeated Braves (38-58), 5-2 | Wrigley Field (34-15) | 62-39 | Won 6 |
| » Starters: Kent Greenfield vs Percy Jones | First | -- |
| Saturday, August 6 |
| » Defeated Dodgers (46-58), 6-2 | Wrigley Field (35-15) | 63-39 | Won 7 |
| » Starters: Dazzy Vance vs Sheriff Blake | First | -- |
| Sunday, August 7 |
| » Defeated Dodgers (46-59), 6-5 | Wrigley Field (36-15) | 64-39 | Won 8 |
| » Starters: Norman Plitt vs Guy Bush | First | -- |
| Tuesday, August 9 |
| » Defeated Dodgers (46-60), 2-0 | Wrigley Field (37-15) | 65-39 | Won 9 |
| » Starters: Jesse Petty vs Hal Carlson | First | -- |
| » Lost to Dodgers (47-60), 5-4 | Wrigley Field (37-16) | 65-40 | |
| » Starters: Bill Doak vs Guy Bush | First | -- |
| Thursday, August 11 |
| » Defeated Reds (49-57), 2-0 | Wrigley Field (38-16) | 66-40 | |
| » Starters: Dolf Luque vs Charlie Root | First | -- |
| Saturday, August 13 |
| » Defeated Reds (49-58), 2-1 | Wrigley Field (39-16) | 67-40 | Won 2 |
| » Starters: Jakie May vs Sheriff Blake | First | -- |
| Sunday, August 14 |
| » Defeated Reds (49-59), 7-2 | Wrigley Field (40-16) | 68-40 | Won 3 |
| » Starters: Red Lucas vs Percy Jones | First | -- |
| Tuesday, August 16 |
| » Defeated Dodgers (47-65), 3-0 | Ebbets Field (7-1) | 69-40 | Won 4 |
| » Starters: Charlie Root vs Doug McWeeny | First | -- |
| Wednesday, August 17 |
| » Lost to Dodgers (48-65), 6-5 | Ebbets Field (7-2) | 69-41 | |
| » Starters: Hal Carlson vs Dazzy Vance | First | -- |
| Friday, August 19 |
| » Defeated Dodgers (48-66), 3-0 | Ebbets Field (8-2) | 70-41 | |
| » Starters: Sheriff Blake vs Jesse Petty | First | -- |
| » Lost to Dodgers (49-66), 6-1 | Ebbets Field (8-3) | 70-42 | |
| » Starters: Percy Jones vs Doug McWeeny | First | -- |
| Saturday, August 20 |
| » Lost to Braves (46-65), 6-5 | Braves Field (6-2) | 70-43 | Lost 2 |
| » Starters: Charlie Root vs Bob Smith | First | -- |
| » Lost to Braves (47-65), 2-1 | Braves Field (6-3) | 70-44 | Lost 3 |
| » Starters: Guy Bush vs Hugh McQuillan | First | -- |
| Monday, August 22 |
| » Lost to Braves (48-65), 5-3 | Braves Field (6-4) | 70-45 | Lost 4 |
| » Starters: Hal Carlson vs Johnny Werts | First | -- |
| Wednesday, August 24 |
| » Lost to Phillies (43-74), 7-6 | Baker Bowl (2-5) | 70-46 | Lost 5 |
| » Starters: Sheriff Blake vs Alex Ferguson | First | -- |
| » Defeated Phillies (43-75), 13-1 | Baker Bowl (3-5) | 71-46 | |
| » Starters: Percy Jones vs Les Sweetland | First | -- |
| Thursday, August 25 |
| » Defeated Phillies (43-76), 8-0 | Baker Bowl (4-5) | 72-46 | Won 2 |
| » Starters: Charlie Root vs Hub Pruett | First | -- |
| Saturday, August 27 |
| » Lost to Phillies (44-76), 2-1 | Baker Bowl (4-6) | 72-47 | |
| » Starters: Guy Bush vs Dutch Ulrich | First | -- |
| » Defeated Phillies (44-77), 10-6 | Baker Bowl (5-6) | 73-47 | |
| » Starters: Jim Brillheart vs Les Sweetland | First | -- |
| Monday, August 29 |
| » Lost to Giants (68-52), 8-7 | Polo Grounds V (3-6) | 73-48 | |
| » Starters: Hal Carlson vs Virgil Barnes | First | -- |
| » Lost to Giants (69-52), 4-1 | Polo Grounds V (3-7) | 73-49 | Lost 2 |
| » Starters: Charlie Root vs Larry Benton | First | -- |
| Tuesday, August 30 |
| » Lost to Giants (70-52), 7-3 | Polo Grounds V (3-8) | 73-50 | Lost 3 |
| » Starters: Percy Jones vs Burleigh Grimes | First | -- |
| Thursday, September 1 |
| » Lost to Pirates (72-50), 4-3 | Forbes Field (7-4) | 73-51 | Lost 4 |
| » Starters: Hal Carlson vs Lee Meadows | Second | 1 out |
| Friday, September 2 |
| » Lost to Reds (56-66), 5-0 | Crosley Field (4-6) | 73-52 | Lost 5 |
| » Starters: Percy Jones vs Jakie May | Second | 1 out |
| Saturday, September 3 |
| » Lost to Reds (57-66), 2-1 | Crosley Field (4-7) | 73-53 | Lost 6 |
| » Starters: Sheriff Blake vs Red Lucas | Third | 2 out |
| Sunday, September 4 |
| » Lost to Cardinals (70-52), 2-1 | Wrigley Field (40-17) | 73-54 | Lost 7 |
| » Starters: Bill Sherdel vs Charlie Root | Third | 3 out |
| » Major-league debuts: Ernie Orsatti (Cardinals) |
| Monday, September 5 |
| » Defeated Cardinals (70-53), 6-1 | Wrigley Field (41-17) | 74-54 | |
| » Starters: Flint Rhem vs Lefty Weinert | Third | 2 out |
| » Lost to Cardinals (71-53), 2-0 | Wrigley Field (41-18) | 74-55 | |
| » Starters: Jesse Haines vs Guy Bush | Third | 2 out |
| Tuesday, September 6 |
| » Lost to Cardinals (72-53), 13-1 | Sportsman's Park III (0-6) | 74-56 | Lost 2 |
| » Starters: Percy Jones vs Pete Alexander | Fourth | 3 out |
| Wednesday, September 7 |
| » Lost to Cardinals (73-53), 6-2 | Sportsman's Park III (0-7) | 74-57 | Lost 3 |
| » Starters: Hal Carlson vs Fred Frankhouse | Fourth | 2½ out |
| » Defeated Cardinals (73-54), 8-4 | Sportsman's Park III (1-7) | 75-57 | |
| » Starters: Sheriff Blake vs Flint Rhem | Fourth | 2½ out |
| Thursday, September 8 |
| » Defeated Cardinals (73-55), 11-7 | Sportsman's Park III (2-7) | 76-57 | Won 2 |
| » Starters: Charlie Root vs Bill Sherdel | Third | 2 out |
| Friday, September 9 |
| » Lost to Giants (76-53), 7-2 | Wrigley Field (41-19) | 76-58 | |
| » Starters: Burleigh Grimes vs Lefty Weinert | Fourth | 3 out |
| Saturday, September 10 |
| » Defeated Giants (76-54), 2-1 | Wrigley Field (42-19) | 77-58 | |
| » Starters: Larry Benton vs Guy Bush | Fourth | 3 out |
| Sunday, September 11 |
| » Defeated Giants (76-55), 7-5 | Wrigley Field (43-19) | 78-58 | Won 2 |
| » Starters: Virgil Barnes vs Hal Carlson | Third | 2½ out |
| Monday, September 12 |
| » Lost to Giants (77-55), 7-5 | Wrigley Field (43-20) | 78-59 | |
| » Starters: Freddie Fitzsimmons vs Charlie Root | Third | 3½ out |
| Tuesday, September 13 |
| » Lost to Dodgers (57-80), 6-5 | Wrigley Field (43-21) | 78-60 | Lost 2 |
| » Starters: Bill Doak vs Sheriff Blake | Third | 5 out |
| Wednesday, September 14 |
| » Lost to Dodgers (58-80), 10-6 | Wrigley Field (43-22) | 78-61 | Lost 3 |
| » Starters: Dazzy Vance vs Percy Jones | Third | 6½ out |
| Future Cub Jim Fanning is born in Chicago, IL. Future Cub Dave Hillman is born in Dungannon, VA. |
| Friday, September 16 |
| » Lost to Dodgers (59-80), 4-3 | Wrigley Field (43-23) | 78-62 | Lost 4 |
| » Starters: Doug McWeeny vs Charlie Root | Fourth | 8 out |
| Saturday, September 17 |
| » Defeated Braves (55-85), 3-2 | Wrigley Field (44-23) | 79-62 | |
| » Starters: Joe Genewich vs Guy Bush | Fourth | 8 out |
| » Defeated Braves (55-86), 5-3 | Wrigley Field (45-23) | 80-62 | Won 2 |
| » Starters: Hal Goldsmith vs Hal Carlson | Fourth | 8 out |
| Sunday, September 18 |
| » Lost to Braves (56-86), 11-7 | Wrigley Field (45-24) | 80-63 | |
| » Starters: Kent Greenfield vs Sheriff Blake | Fourth | 8½ out |
| Monday, September 19 |
| » Defeated Braves (56-87), 6-0 | Wrigley Field (46-24) | 81-63 | |
| » Starters: Charlie Robertson vs Art Nehf | Fourth | 7½ out |
| Tuesday, September 20 |
| » Defeated Braves (56-88), 8-5 | Wrigley Field (47-24) | 82-63 | Won 2 |
| » Starters: Guy Morrison vs Lefty Weinert | Third | 6½ out |
| Thursday, September 22 |
| » Defeated Phillies (48-95), 8-4 | Wrigley Field (48-24) | 83-63 | Won 3 |
| » Starters: Hub Pruett vs Charlie Root | Fourth | 6½ out |
| Friday, September 23 |
| » Defeated Phillies (48-96), 10-0 | Wrigley Field (49-24) | 84-63 | Won 4 |
| » Starters: Alex Ferguson vs Hal Carlson | Fourth | 5½ out |
| Saturday, September 24 |
| » Defeated Phillies (48-97), 10-2 | Wrigley Field (50-24) | 85-63 | Won 5 |
| » Starters: Russ Miller vs Sheriff Blake | Fourth | 4½ out |
| » Major-league debuts: Russ Miller (Phillies) |
| Sunday, September 25 |
| » Lost to Pirates (90-58), 2-1 | Wrigley Field (50-25) | 85-64 | |
| » Starters: Vic Aldridge vs Guy Bush | Fourth | 6½ out |
| » Lost to Pirates (91-58), 6-1 | Wrigley Field (50-26) | 85-65 | Lost 2 |
| » Starters: Ray Kremer vs Charlie Root | Fourth | 6½ out |
| Monday, September 26 |
| » Lost to Pirates (92-58), 1-0 | Wrigley Field (50-27) | 85-66 | Lost 3 |
| » Starters: Johnny Miljus vs Art Nehf | Fourth | 7½ out |
| Tuesday, September 27 |
| » Lost to Pirates (93-58), 2-1 | Wrigley Field (50-28) | 85-67 | Lost 4 |
| » Starters: Lee Meadows vs Hal Carlson | Fourth | 8½ out |
| Sunday, October 2 |
| » Lost to Cardinals (92-61), 6-4 | Sportsman's Park III (2-8) | 85-68 | Lost 5 |
| » Starters: Guy Bush vs Jesse Haines | Fourth | 8½ out |
| Tuesday, October 4 |
| Future Cub Bob Kelly is born in Cleveland, OH. |
| Saturday, October 15 |
| Future Cub Bill Henry is born in Alice, TX. |
| Monday, October 17 |
| Future Cub Johnny Klippstein is born in Washington, DC. |
| Friday, November 4 |
| Future Cub Carl Sawatski is born in Shickshinny, PA. |
| Tuesday, December 6 |
| Future Cub Tommy Brown is born in Brooklyn, NY. |
Game information provided by Retrosheet (www.retrosheet.org) |