| Tuesday, January 10 |
| Future Cub Dan Rohn is born in Alpena, MI. Former Cub Algie McBride dies in Georgetown, OH at the age of 87. |
| Wednesday, February 8 |
| Former Cub Long Tom Hughes dies in Chicago, IL at the age of 78. |
| Saturday, February 25 |
| Future Cub Ed Lynch is born in Brooklyn, NY. |
| Friday, March 2 |
| Former Cub Fred Merkle dies in Daytona Beach, FL at the age of 68. |
| Saturday, March 10 |
| Former Cub Solly Hofman dies in St.Louis, MO at the age of 74. |
| Tuesday, April 10 |
| Former Cub Ginger Beaumont dies in Burlington, WI at the age of 80. |
| Tuesday, April 17 |
| » Lost to Braves (1-0), 6-0 | County Stadium (0-1) | 0-1 | |
| » Starters: Bob Rush vs Lew Burdette | Second | 1 out |
| Wednesday, April 18 |
| » Major-league debuts: Hal Griggs and Herb Plews (Senators) |
| Thursday, April 19 |
| » Lost to Braves (2-0), 3-1 | County Stadium (0-2) | 0-2 | Lost 2 |
| » Starters: Warren Hacker vs Bob Buhl | Fifth | 2 out |
| » Major-league debuts: Wes Covington (Braves) |
| Friday, April 20 |
| » Defeated Reds (1-2), 12-1 | Wrigley Field (1-0) | 1-2 | |
| » Starters: Art Fowler vs Sam Jones | Fourth | 2 out |
| » Major-league debuts: Tom Acker (Reds) |
| Saturday, April 21 |
| » Defeated Reds (1-3), 3-2 | Wrigley Field (2-0) | 2-2 | Won 2 |
| » Starters: Johnny Klippstein vs Russ Meyer | Third | 1 out |
| Sunday, April 22 |
| » Defeated Reds (1-4), 5-4 | Wrigley Field (3-0) | 3-2 | Won 3 |
| » Starters: Joe Nuxhall vs Paul Minner | Second | ½ out |
| » Tied Reds, 1-1 | Wrigley Field (3-0) | 3-2 | |
| » Starters: Brooks Lawrence vs Bob Rush | Second | ½ out |
| Wednesday, April 25 |
| » Lost to Cardinals (5-3), 6-0 | Sportsman's Park III (0-1) | 3-3 | |
| » Starters: Sam Jones vs Harvey Haddix | Fourth | 1½ out |
| Friday, April 27 |
| » Lost to Reds (2-5), 7-4 | Crosley Field (0-1) | 3-4 | Lost 2 |
| » Starters: Russ Meyer vs Johnny Klippstein | Fifth | 2½ out |
| Saturday, April 28 |
| » Lost to Reds (3-5), 9-1 | Crosley Field (0-2) | 3-5 | Lost 3 |
| » Starters: Paul Minner vs Brooks Lawrence | Fifth | 3½ out |
| Sunday, April 29 |
| » Lost to Reds (4-5), 5-4 | Crosley Field (0-3) | 3-6 | Lost 4 |
| » Starters: Bob Rush vs Joe Nuxhall | Sixth | 3 out |
| » Lost to Reds (5-5), 8-4 | Crosley Field (0-4) | 3-7 | Lost 5 |
| » Starters: Sam Jones vs Art Fowler | Sixth | 3 out |
| Tuesday, May 1 |
| » Lost to Giants (6-6), 2-1 | Wrigley Field (3-1) | 3-8 | Lost 6 |
| » Starters: Jim Hearn vs Warren Hacker | Seventh | 3½ out |
| Wednesday, May 2 |
| » Lost to Giants (7-6), 6-5 | Wrigley Field (3-2) | 3-9 | Lost 7 |
| » Starters: Al Worthington vs Russ Meyer | Seventh | 4½ out |
| Friday, May 4 |
| » Defeated Phillies (5-8), 2-1 | Wrigley Field (4-2) | 4-9 | |
| » Starters: Robin Roberts vs Bob Rush | Eighth | 4 out |
| Sunday, May 6 |
| » Lost to Pirates (8-9), 2-1 | Wrigley Field (4-3) | 4-10 | |
| » Starters: Ron Kline vs Paul Minner | Seventh | 4½ out |
| » Tied Pirates, 6-6 | Wrigley Field (4-3) | 4-10 | |
| » Starters: Bob Friend vs Sam Jones | Seventh | 4½ out |
| Tuesday, May 8 |
| » Lost to Dodgers (9-9), 6-0 | Wrigley Field (4-4) | 4-11 | Lost 2 |
| » Starters: Don Newcombe vs Warren Hacker | Seventh | 6 out |
| Saturday, May 12 |
| » Defeated Cardinals (13-7), 14-10 | Wrigley Field (5-4) | 5-11 | |
| » Starters: Vinegar Bend Mizell vs Bob Rush | Seventh | 5½ out |
| Sunday, May 13 |
| » Lost to Cardinals (14-7), 3-2 | Wrigley Field (5-5) | 5-12 | |
| » Starters: Murry Dickson vs Paul Minner | Eighth | 7½ out |
| » Lost to Cardinals (15-7), 14-7 | Wrigley Field (5-6) | 5-13 | Lost 2 |
| » Starters: Lindy McDaniel vs Sam Jones | Eighth | 7½ out |
| Tuesday, May 15 |
| » Lost to Giants (10-13), 6-4 | Polo Grounds V (0-1) | 5-14 | Lost 3 |
| » Starters: Warren Hacker vs Johnny Antonelli | Eighth | 7½ out |
| Wednesday, May 16 |
| » Lost to Giants (11-13), 9-3 | Polo Grounds V (0-2) | 5-15 | Lost 4 |
| » Starters: Bob Rush vs Don Liddle | Eighth | 7½ out |
| Thursday, May 17 |
| » Defeated Pirates (12-12), 4-1 | Forbes Field (1-0) | 6-15 | |
| » Starters: Russ Meyer vs Ron Kline | Eighth | 7½ out |
| Friday, May 18 |
| » Defeated Pirates (12-13), 3-2 | Forbes Field (2-0) | 7-15 | Won 2 |
| » Starters: Paul Minner vs Vern Law | Eighth | 7 out |
| Saturday, May 19 |
| » Lost to Pirates (13-13), 7-4 | Forbes Field (2-1) | 7-16 | |
| » Starters: Sam Jones vs Red Munger | Eighth | 8 out |
| Future Cub Luis Salazar is born in Barcelona, Venezuela. |
| Sunday, May 20 |
| » Lost to Dodgers (15-11), 5-3 | Ebbets Field (0-1) | 7-17 | Lost 2 |
| » Starters: Jim Brosnan vs Don Drysdale | Eighth | 8 out |
| » Lost to Dodgers (16-11), 5-3 | Ebbets Field (0-2) | 7-18 | Lost 3 |
| » Starters: Bob Rush vs Ken Lehman | Eighth | 8 out |
| Wednesday, May 23 |
| » Defeated Phillies (10-19), 5-4 | Shibe Park (1-0) | 8-18 | |
| » Starters: Warren Hacker vs Harvey Haddix | Eighth | 8 out |
| Friday, May 25 |
| » Lost to Cardinals (20-13), 6-1 | Sportsman's Park III (0-2) | 8-19 | |
| » Starters: Russ Meyer vs Murry Dickson | Eighth | 8 out |
| Sunday, May 27 |
| » Lost to Cardinals (21-13), 11-9 | Sportsman's Park III (0-3) | 8-20 | Lost 2 |
| » Starters: Paul Minner vs Tom Poholsky | Seventh | 10 out |
| » Lost to Cardinals (22-13), 12-2 | Sportsman's Park III (0-4) | 8-21 | Lost 3 |
| » Starters: Jim Brosnan vs Vinegar Bend Mizell | Seventh | 10 out |
| Monday, May 28 |
| » Defeated Reds (18-15), 4-1 | Wrigley Field (6-6) | 9-21 | |
| » Starters: Joe Nuxhall vs Bob Rush | Eighth | 10 out |
| Future Cub Randy Martz is born in Harrisburg, PA. |
| Tuesday, May 29 |
| » Lost to Reds (19-15), 10-4 | Wrigley Field (6-7) | 9-22 | |
| » Starters: Brooks Lawrence vs Sam Jones | Seventh | 10½ out |
| Wednesday, May 30 |
| » Defeated Braves (17-10), 10-9 | Wrigley Field (7-7) | 10-22 | |
| » Starters: Bob Buhl vs Russ Meyer | Eighth | 10½ out |
| » Lost to Braves (18-10), 11-9 | Wrigley Field (7-8) | 10-23 | |
| » Starters: Ray Crone vs Warren Hacker | Eighth | 10½ out |
| Thursday, May 31 |
| » Lost to Braves (19-10), 15-8 | Wrigley Field (7-9) | 10-24 | Lost 2 |
| » Starters: Lew Burdette vs Paul Minner | Seventh | 11½ out |
| Friday, June 1 |
| » Defeated Dodgers (19-17), 4-2 | Wrigley Field (8-9) | 11-24 | |
| » Starters: Roger Craig vs Jim Brosnan | Eighth | 10½ out |
| Saturday, June 2 |
| » Defeated Dodgers (19-18), 8-1 | Wrigley Field (9-9) | 12-24 | Won 2 |
| » Starters: Carl Erskine vs Don Kaiser | Eighth | 9 out |
| » Defeated Dodgers (19-19), 5-4 | Wrigley Field (10-9) | 13-24 | Won 3 |
| » Starters: Don Newcombe vs Bob Rush | Eighth | 9 out |
| Sunday, June 3 |
| » Lost to Dodgers (20-19), 4-3 | Wrigley Field (10-10) | 13-25 | |
| » Starters: Sandy Koufax vs Russ Meyer | Eighth | 9½ out |
| Tuesday, June 5 |
| » Defeated Pirates (24-18), 7-3 | Wrigley Field (11-10) | 14-25 | |
| » Starters: Bob Friend vs Warren Hacker | Eighth | 9 out |
| Wednesday, June 6 |
| » Lost to Pirates (25-18), 8-2 | Wrigley Field (11-11) | 14-26 | |
| » Starters: Ron Kline vs Paul Minner | Eighth | 10 out |
| Thursday, June 7 |
| » Defeated Pirates (25-19), 5-2 | Wrigley Field (12-11) | 15-26 | |
| » Starters: Roy Face vs Bob Rush | Eighth | 10 out |
| Friday, June 8 |
| » Defeated Phillies (16-28), 5-4 | Wrigley Field (13-11) | 16-26 | Won 2 |
| » Starters: Robin Roberts vs Don Kaiser | Seventh | 10 out |
| Saturday, June 9 |
| » Lost to Phillies (17-28), 6-4 | Wrigley Field (13-12) | 16-27 | |
| » Starters: Saul Rogovin vs Russ Meyer | Eighth | 10 out |
| Sunday, June 10 |
| » Defeated Phillies (17-29), 2-1 | Wrigley Field (14-12) | 17-27 | |
| » Starters: Curt Simmons vs Warren Hacker | Seventh | 8½ out |
| » Defeated Phillies (17-30), 5-2 | Wrigley Field (15-12) | 18-27 | Won 2 |
| » Starters: Jim Owens vs Sam Jones | Seventh | 8½ out |
| Tuesday, June 12 |
| » Defeated Giants (19-28), 8-5 | Wrigley Field (16-12) | 19-27 | Won 3 |
| » Starters: Al Worthington vs Paul Minner | Fifth | 7½ out |
| Wednesday, June 13 |
| » Defeated Giants (19-29), 6-5 | Wrigley Field (17-12) | 20-27 | Won 4 |
| » Starters: Jim Hearn vs Bob Rush | Fifth | 7 out |
| Thursday, June 14 |
| » Major-league debuts: Ed Bressoud (Giants) |
| Friday, June 15 |
| » Lost to Phillies (20-31), 6-5 | Shibe Park (1-1) | 20-28 | |
| » Starters: Don Kaiser vs Saul Rogovin | Sixth | 7½ out |
| » Defeated Phillies (20-32), 8-5 | Shibe Park (2-1) | 21-28 | |
| » Starters: Warren Hacker vs Curt Simmons | Sixth | 7½ out |
| Sunday, June 17 |
| » Lost to Phillies (21-32), 7-1 | Shibe Park (2-2) | 21-29 | |
| » Starters: Warren Hacker vs Robin Roberts | Fifth | 7 out |
| » Defeated Phillies (21-33), 7-4 | Shibe Park (3-2) | 22-29 | |
| » Starters: Sam Jones vs Stu Miller | Fifth | 7 out |
| Tuesday, June 19 |
| » Lost to Giants (22-32), 2-0 | Polo Grounds V (0-3) | 22-30 | |
| » Starters: Bob Rush vs Johnny Antonelli | Sixth | 7½ out |
| Wednesday, June 20 |
| » Lost to Giants (23-32), 4-1 | Polo Grounds V (0-4) | 22-31 | Lost 2 |
| » Starters: Don Kaiser vs Al Worthington | Seventh | 8 out |
| Thursday, June 21 |
| » Major-league debuts: Felix Mantilla (Braves) |
| Future Cub Rick Sutcliffe is born in Independence, MO. |
| Saturday, June 23 |
| » Defeated Pirates (30-28), 9-5 | Forbes Field (3-1) | 23-31 | |
| » Starters: Warren Hacker vs Bob Friend | Sixth | 9 out |
| Sunday, June 24 |
| » Defeated Pirates (30-29), 5-3 | Forbes Field (4-1) | 24-31 | Won 2 |
| » Starters: Bob Rush vs Vern Law | Sixth | 10 out |
| » Lost to Pirates (31-29), 1-0 | Forbes Field (4-2) | 24-32 | |
| » Starters: Sam Jones vs Laurin Pepper | Sixth | 10 out |
| Monday, June 25 |
| » Lost to Dodgers (33-27), 3-2 | Roosevelt Stadium (0-1) | 24-33 | Lost 2 |
| » Starters: Don Kaiser vs Carl Erskine | Sixth | 11 out |
| Tuesday, June 26 |
| » Lost to Dodgers (34-27), 10-5 | Ebbets Field (0-3) | 24-34 | Lost 3 |
| » Starters: Jim Davis vs Sal Maglie | Seventh | 11 out |
| Wednesday, June 27 |
| » Lost to Dodgers (35-27), 6-2 | Ebbets Field (0-4) | 24-35 | Lost 4 |
| » Starters: Warren Hacker vs Roger Craig | Seventh | 11 out |
| Friday, June 29 |
| » Defeated Braves (35-25), 8-4 | Wrigley Field (18-12) | 25-35 | |
| » Starters: Lew Burdette vs Bob Rush | Seventh | 10 out |
| Saturday, June 30 |
| » Lost to Braves (36-25), 4-3 | Wrigley Field (18-13) | 25-36 | |
| » Starters: Gene Conley vs Sam Jones | Sixth | 11 out |
| Sunday, July 1 |
| » Defeated Braves (36-26), 7-0 | Wrigley Field (19-13) | 26-36 | |
| » Starters: Bob Buhl vs Don Kaiser | Eighth | 11 out |
| » Lost to Braves (37-26), 4-3 | Wrigley Field (19-14) | 26-37 | |
| » Starters: Ray Crone vs Jim Davis | Eighth | 11 out |
| » Major-league debuts: Jerry Kindall (Cubs) |
| Monday, July 2 |
| » Defeated Cardinals (36-34), 6-3 | Wrigley Field (20-14) | 27-37 | |
| » Starters: Tom Poholsky vs Warren Hacker | Eighth | 11 out |
| Tuesday, July 3 |
| » Defeated Cardinals (36-35), 7-4 | Wrigley Field (21-14) | 28-37 | Won 2 |
| » Starters: Vinegar Bend Mizell vs Jim Davis | Seventh | 10 out |
| Wednesday, July 4 |
| » Defeated Reds (40-30), 5-4 | Crosley Field (1-4) | 29-37 | Won 3 |
| » Starters: Bob Rush vs Art Fowler | Sixth | 10 out |
| » Lost to Reds (41-30), 4-3 | Crosley Field (1-5) | 29-38 | |
| » Starters: Sam Jones vs Brooks Lawrence | Sixth | 10 out |
| Thursday, July 5 |
| » Defeated Braves (39-29), 7-1 | County Stadium (1-2) | 30-38 | |
| » Starters: Vito Valentinetti vs Ray Crone | Sixth | 9½ out |
| Friday, July 6 |
| » Lost to Braves (40-29), 5-0 | County Stadium (1-3) | 30-39 | |
| » Starters: Don Kaiser vs Warren Spahn | Sixth | 10½ out |
| Saturday, July 7 |
| » Lost to Braves (41-29), 5-0 | County Stadium (1-4) | 30-40 | Lost 2 |
| » Starters: Warren Hacker vs Lew Burdette | Sixth | 11½ out |
| Sunday, July 8 |
| » Defeated Braves (41-30), 10-6 | County Stadium (2-4) | 31-40 | |
| » Starters: Bob Rush vs Bob Buhl | Sixth | 11½ out |
| Monday, July 9 |
| Future Cub Guy Hoffman is born in Ottawa, IL. |
| Thursday, July 12 |
| » Lost to Pirates (36-38), 2-1 | Wrigley Field (21-15) | 31-41 | |
| » Starters: Ron Kline vs Don Kaiser | Seventh | 12 out |
| » Lost to Pirates (37-38), 5-4 | Wrigley Field (21-16) | 31-42 | Lost 2 |
| » Starters: Cholly Naranjo vs Sam Jones | Seventh | 12 out |
| Friday, July 13 |
| » Defeated Pirates (37-39), 7-6 | Wrigley Field (22-16) | 32-42 | |
| » Starters: Bob Friend vs Warren Hacker | Seventh | 12 out |
| Future Cub Bill Caudill is born in Santa Monica, CA. |
| Saturday, July 14 |
| » Defeated Pirates (37-40), 6-2 | Wrigley Field (23-16) | 33-42 | Won 2 |
| » Starters: Vern Law vs Bob Rush | Seventh | 11½ out |
| » Defeated Pirates (37-41), 6-5 | Wrigley Field (24-16) | 34-42 | Won 3 |
| » Starters: Red Munger vs Jim Davis | Seventh | 11½ out |
| Sunday, July 15 |
| » Lost to Dodgers (43-36), 10-8 | Wrigley Field (24-17) | 34-43 | |
| » Starters: Don Newcombe vs Jim Brosnan | Seventh | 13 out |
| Monday, July 16 |
| » Lost to Dodgers (44-36), 4-1 | Wrigley Field (24-18) | 34-44 | Lost 2 |
| » Starters: Roger Craig vs Sam Jones | Sixth | 14 out |
| Tuesday, July 17 |
| » Defeated Phillies (37-45), 3-2 | Wrigley Field (25-18) | 35-44 | |
| » Starters: Ron Negray vs Don Kaiser | Seventh | 13 out |
| Wednesday, July 18 |
| » Lost to Phillies (38-45), 6-4 | Wrigley Field (25-19) | 35-45 | |
| » Starters: Robin Roberts vs Warren Hacker | Seventh | 14½ out |
| » Lost to Phillies (39-45), 6-1 | Wrigley Field (25-20) | 35-46 | Lost 2 |
| » Starters: Curt Simmons vs Jim Davis | Seventh | 14½ out |
| Thursday, July 19 |
| » Defeated Phillies (39-46), 4-3 | Wrigley Field (26-20) | 36-46 | |
| » Starters: Saul Rogovin vs Bob Rush | Seventh | 14½ out |
| Friday, July 20 |
| » Defeated Giants (32-50), 7-4 | Wrigley Field (27-20) | 37-46 | Won 2 |
| » Starters: Windy McCall vs Jim Brosnan | Seventh | 14½ out |
| Sunday, July 22 |
| » Defeated Giants (32-51), 4-1 | Wrigley Field (28-20) | 38-46 | Won 3 |
| » Starters: Johnny Antonelli vs Don Kaiser | Sixth | 14 out |
| » Defeated Giants (32-52), 2-1 | Wrigley Field (29-20) | 39-46 | Won 4 |
| » Starters: Joe Margoneri vs Sam Jones | Sixth | 14 out |
| Future Cub Scott Sanderson is born in Dearborn, MI. |
| Tuesday, July 24 |
| » Lost to Pirates (41-47), 6-2 | Forbes Field (4-3) | 39-47 | |
| » Starters: Bob Rush vs Ron Kline | Seventh | 15 out |
| Wednesday, July 25 |
| » Lost to Pirates (42-47), 9-8 | Forbes Field (4-4) | 39-48 | Lost 2 |
| » Starters: Warren Hacker vs Bob Friend | Seventh | 16 out |
| Thursday, July 26 |
| » Lost to Pirates (43-47), 4-0 | Forbes Field (4-5) | 39-49 | Lost 3 |
| » Starters: Sam Jones vs Fred Waters | Seventh | 17 out |
| Friday, July 27 |
| » Lost to Dodgers (52-39), 4-3 | Ebbets Field (0-5) | 39-50 | Lost 4 |
| » Starters: Don Kaiser vs Carl Erskine | Seventh | 17 out |
| Saturday, July 28 |
| » Lost to Dodgers (53-39), 6-3 | Ebbets Field (0-6) | 39-51 | Lost 5 |
| » Starters: Jim Hughes vs Sal Maglie | Seventh | 17½ out |
| Sunday, July 29 |
| » Lost to Dodgers (54-39), 1-0 | Ebbets Field (0-7) | 39-52 | Lost 6 |
| » Starters: Jim Davis vs Don Newcombe | Sixth | 17 out |
| » Defeated Dodgers (54-40), 4-2 | Ebbets Field (1-7) | 40-52 | |
| » Starters: Bob Rush vs Sandy Koufax | Sixth | 17 out |
| Monday, July 30 |
| » Lost to Phillies (44-51), 5-4 | Shibe Park (3-3) | 40-53 | |
| » Starters: Vito Valentinetti vs Robin Roberts | Seventh | 18½ out |
| » Lost to Phillies (45-51), 4-2 | Shibe Park (3-4) | 40-54 | Lost 2 |
| » Starters: Warren Hacker vs Harvey Haddix | Seventh | 18½ out |
| Tuesday, July 31 |
| » Defeated Phillies (45-52), 9-4 | Shibe Park (4-4) | 41-54 | |
| » Starters: Sam Jones vs Stu Miller | Seventh | 17½ out |
| Wednesday, August 1 |
| » Lost to Phillies (46-52), 10-8 | Shibe Park (4-5) | 41-55 | |
| » Starters: Don Kaiser vs Saul Rogovin | Seventh | 17½ out |
| Friday, August 3 |
| » Lost to Giants (36-59), 7-1 | Polo Grounds V (0-5) | 41-56 | Lost 2 |
| » Starters: Don Kaiser vs Jim Hearn | Seventh | 16½ out |
| » Defeated Giants (36-60), 2-0 | Polo Grounds V (1-5) | 42-56 | |
| » Starters: Bob Rush vs Dick Littlefield | Seventh | 16½ out |
| Saturday, August 4 |
| » Lost to Giants (37-60), 3-2 | Polo Grounds V (1-6) | 42-57 | |
| » Starters: Warren Hacker vs Joe Margoneri | Seventh | 17½ out |
| Monday, August 6 |
| » Defeated Braves (60-39), 5-4 | County Stadium (3-4) | 43-57 | |
| » Starters: Sam Jones vs Ray Crone | Seventh | 17½ out |
| Tuesday, August 7 |
| » Lost to Braves (61-39), 6-1 | County Stadium (3-5) | 43-58 | |
| » Starters: Jim Brosnan vs Warren Spahn | Seventh | 18½ out |
| » Major-league debuts: Moe Drabowsky (Cubs) |
| Wednesday, August 8 |
| » Lost to Reds (61-44), 8-2 | Crosley Field (1-6) | 43-59 | Lost 2 |
| » Starters: Bob Rush vs Johnny Klippstein | Seventh | 19 out |
| Thursday, August 9 |
| » Lost to Reds (62-44), 5-3 | Crosley Field (1-7) | 43-60 | Lost 3 |
| » Starters: Don Kaiser vs Joe Nuxhall | Seventh | 19½ out |
| Friday, August 10 |
| » Lost to Cardinals (54-53), 4-3 | Wrigley Field (29-21) | 43-61 | Lost 4 |
| » Starters: Vinegar Bend Mizell vs Warren Hacker | Seventh | 19½ out |
| Saturday, August 11 |
| » Lost to Cardinals (55-53), 3-1 | Wrigley Field (29-22) | 43-62 | Lost 5 |
| » Starters: Willard Schmidt vs Sam Jones | Seventh | 20½ out |
| Sunday, August 12 |
| » Defeated Cardinals (55-54), 6-2 | Wrigley Field (30-22) | 44-62 | |
| » Starters: Bob Blaylock vs Bob Rush | Seventh | 20½ out |
| » Tied Cardinals, 0-0 | Wrigley Field (30-22) | 44-62 | |
| » Starters: Herm Wehmeier vs Jim Davis | Seventh | 20½ out |
| Tuesday, August 14 |
| » Lost to Reds (64-47), 2-0 | Wrigley Field (30-23) | 44-63 | |
| » Starters: Joe Nuxhall vs Don Kaiser | Seventh | 21 out |
| Wednesday, August 15 |
| » Lost to Reds (65-47), 4-3 | Wrigley Field (30-24) | 44-64 | Lost 2 |
| » Starters: Hal Jeffcoat vs Warren Hacker | Seventh | 22½ out |
| » Lost to Reds (66-47), 7-3 | Wrigley Field (30-25) | 44-65 | Lost 3 |
| » Starters: Art Fowler vs Russ Meyer | Seventh | 22½ out |
| Thursday, August 16 |
| » Defeated Reds (66-48), 4-2 | Wrigley Field (31-25) | 45-65 | |
| » Starters: Brooks Lawrence vs Sam Jones | Seventh | 22½ out |
| Friday, August 17 |
| » Lost to Cardinals (57-56), 2-1 | Sportsman's Park III (0-5) | 45-66 | |
| » Starters: Bob Rush vs Herm Wehmeier | Seventh | 22½ out |
| Saturday, August 18 |
| » Defeated Cardinals (57-57), 8-1 | Sportsman's Park III (1-5) | 46-66 | |
| » Starters: Moe Drabowsky vs Willard Schmidt | Seventh | 21½ out |
| Sunday, August 19 |
| » Lost to Cardinals (58-57), 6-0 | Sportsman's Park III (1-6) | 46-67 | |
| » Starters: Don Kaiser vs Murry Dickson | Seventh | 22 out |
| » Defeated Cardinals (58-58), 3-1 | Sportsman's Park III (2-6) | 47-67 | |
| » Starters: Jim Davis vs Vinegar Bend Mizell | Seventh | 22 out |
| Tuesday, August 21 |
| » Defeated Phillies (55-60), 6-4 | Wrigley Field (32-25) | 48-67 | Won 2 |
| » Starters: Robin Roberts vs Sam Jones | Seventh | 23 out |
| Wednesday, August 22 |
| » Defeated Phillies (55-61), 8-3 | Wrigley Field (33-25) | 49-67 | Won 3 |
| » Starters: Harvey Haddix vs Bob Rush | Seventh | 22 out |
| Thursday, August 23 |
| » Lost to Giants (46-70), 2-1 | Wrigley Field (33-26) | 49-68 | |
| » Starters: Johnny Antonelli vs Moe Drabowsky | Seventh | 23½ out |
| » Lost to Giants (47-70), 8-5 | Wrigley Field (33-27) | 49-69 | Lost 2 |
| » Starters: Max Surkont vs Warren Hacker | Seventh | 23½ out |
| Friday, August 24 |
| » Lost to Giants (48-70), 5-4 | Wrigley Field (33-28) | 49-70 | Lost 3 |
| » Starters: Ruben Gomez vs Don Kaiser | Seventh | 24½ out |
| Saturday, August 25 |
| » Lost to Giants (49-70), 6-0 | Wrigley Field (33-29) | 49-71 | Lost 4 |
| » Starters: Steve Ridzik vs Jim Davis | Eighth | 24½ out |
| Sunday, August 26 |
| » Lost to Pirates (52-72), 2-0 | Wrigley Field (33-30) | 49-72 | Lost 5 |
| » Starters: Bob Friend vs Bob Rush | Eighth | 26 out |
| » Lost to Pirates (53-72), 2-1 | Wrigley Field (33-31) | 49-73 | Lost 6 |
| » Starters: Ron Kline vs Sam Jones | Eighth | 26 out |
| Tuesday, August 28 |
| » Lost to Dodgers (73-49), 6-4 | Wrigley Field (33-32) | 49-74 | Lost 7 |
| » Starters: Sal Maglie vs Moe Drabowsky | Eighth | 25 out |
| » Defeated Dodgers (73-50), 4-3 | Wrigley Field (34-32) | 50-74 | |
| » Starters: Don Drysdale vs Jim Brosnan | Eighth | 25 out |
| Wednesday, August 29 |
| » Lost to Dodgers (74-50), 11-4 | Wrigley Field (34-33) | 50-75 | |
| » Starters: Carl Erskine vs Don Kaiser | Eighth | 26 out |
| Thursday, August 30 |
| » Defeated Dodgers (74-51), 4-3 | Wrigley Field (35-33) | 51-75 | |
| » Starters: Roger Craig vs Jim Davis | Eighth | 25½ out |
| Friday, August 31 |
| » Lost to Reds (75-53), 4-3 | Crosley Field (1-8) | 51-76 | |
| » Starters: Bob Rush vs Hal Jeffcoat | Eighth | 27 out |
| Saturday, September 1 |
| » Lost to Reds (76-53), 7-3 | Crosley Field (1-9) | 51-77 | Lost 2 |
| » Starters: Sam Jones vs Brooks Lawrence | Seventh | 28 out |
| Sunday, September 2 |
| » Lost to Reds (77-53), 3-2 | Crosley Field (1-10) | 51-78 | Lost 3 |
| » Starters: Moe Drabowsky vs Joe Nuxhall | Seventh | 29 out |
| Monday, September 3 |
| » Lost to Cardinals (64-67), 4-2 | Sportsman's Park III (2-7) | 51-79 | Lost 4 |
| » Starters: Don Kaiser vs Murry Dickson | Seventh | 29 out |
| » Defeated Cardinals (64-68), 8-0 | Sportsman's Park III (3-7) | 52-79 | |
| » Starters: Jim Brosnan vs Lindy McDaniel | Seventh | 29 out |
| Tuesday, September 4 |
| Former Cub Pat Ragan dies in Los Angeles, CA at the age of 68. |
| Wednesday, September 5 |
| » Lost to Cardinals (65-68), 2-1 | Sportsman's Park III (3-8) | 52-80 | |
| » Starters: Bob Rush vs Herm Wehmeier | Eighth | 28½ out |
| Friday, September 7 |
| » Defeated Braves (81-53), 5-0 | Wrigley Field (36-33) | 53-80 | |
| » Starters: Bob Buhl vs Sam Jones | Seventh | 27½ out |
| Saturday, September 8 |
| » Defeated Braves (81-54), 2-1 | Wrigley Field (37-33) | 54-80 | Won 2 |
| » Starters: Lew Burdette vs Moe Drabowsky | Eighth | 26½ out |
| Sunday, September 9 |
| » Lost to Braves (82-54), 7-4 | Wrigley Field (37-34) | 54-81 | |
| » Starters: Warren Spahn vs Don Kaiser | Eighth | 28½ out |
| » Lost to Braves (83-54), 5-3 | Wrigley Field (37-35) | 54-82 | Lost 2 |
| » Starters: Gene Conley vs Jim Brosnan | Eighth | 28½ out |
| Tuesday, September 11 |
| » Lost to Pirates (61-78), 4-3 | Forbes Field (4-6) | 54-83 | Lost 3 |
| » Starters: Bob Rush vs Dick Hall | Seventh | 28½ out |
| Wednesday, September 12 |
| » Defeated Pirates (61-79), 3-0 | Forbes Field (5-6) | 55-83 | |
| » Starters: Sam Jones vs Vern Law | Eighth | 28½ out |
| Friday, September 14 |
| » Lost to Dodgers (84-56), 4-2 | Ebbets Field (1-8) | 55-84 | |
| » Starters: Moe Drabowsky vs Roger Craig | Eighth | 29½ out |
| Saturday, September 15 |
| » Lost to Dodgers (85-56), 3-0 | Ebbets Field (1-9) | 55-85 | Lost 2 |
| » Starters: Don Kaiser vs Don Newcombe | Eighth | 29½ out |
| Sunday, September 16 |
| » Defeated Phillies (65-76), 7-4 | Shibe Park (5-5) | 56-85 | |
| » Starters: Warren Hacker vs Saul Rogovin | Eighth | 30 out |
| » Lost to Phillies (66-76), 4-1 | Shibe Park (5-6) | 56-86 | |
| » Starters: Sam Jones vs Jack Sanford | Eighth | 30 out |
| » Major-league debuts: Jack Sanford (Phillies) |
| Monday, September 17 |
| Future Cub Thad Bosley is born in Oceanside, CA. |
| Tuesday, September 18 |
| » Defeated Giants (59-85), 4-2 | Polo Grounds V (2-6) | 57-86 | |
| » Starters: Bob Rush vs Ruben Gomez | Eighth | 30 out |
| » Lost to Giants (60-85), 8-2 | Polo Grounds V (2-7) | 57-87 | |
| » Starters: Jim Brosnan vs Steve Ridzik | Eighth | 30 out |
| Wednesday, September 19 |
| » Lost to Giants (61-85), 7-2 | Polo Grounds V (2-8) | 57-88 | Lost 2 |
| » Starters: Moe Drabowsky vs Joe Margoneri | Eighth | 31½ out |
| » Lost to Giants (62-85), 3-2 | Polo Grounds V (2-9) | 57-89 | Lost 3 |
| » Starters: Dave Hillman vs Dick Littlefield | Eighth | 31½ out |
| Friday, September 21 |
| » Lost to Braves (89-59), 6-4 | County Stadium (3-6) | 57-90 | Lost 4 |
| » Starters: Warren Hacker vs Warren Spahn | Eighth | 31½ out |
| Saturday, September 22 |
| » Defeated Braves (89-60), 5-4 | County Stadium (4-6) | 58-90 | |
| » Starters: Sam Jones vs Lew Burdette | Eighth | 30½ out |
| Sunday, September 23 |
| » Lost to Braves (90-60), 7-4 | County Stadium (4-7) | 58-91 | |
| » Starters: Bob Rush vs Bob Buhl | Eighth | 31½ out |
| Tuesday, September 25 |
| » Lost to Cardinals (74-75), 5-1 | Wrigley Field (37-36) | 58-92 | Lost 2 |
| » Starters: Lindy McDaniel vs Dave Hillman | Eighth | 32 out |
| » Defeated Cardinals (74-76), 6-2 | Wrigley Field (38-36) | 59-92 | |
| » Starters: Bob Blaylock vs Don Kaiser | Eighth | 32 out |
| Wednesday, September 26 |
| » Defeated Cardinals (74-77), 3-2 | Wrigley Field (39-36) | 60-92 | Won 2 |
| » Starters: Murry Dickson vs Jim Davis | Eighth | 31½ out |
| Saturday, September 29 |
| » Lost to Reds (90-63), 9-6 | Wrigley Field (39-37) | 60-93 | |
| » Starters: Joe Nuxhall vs Sam Jones | Eighth | 32 out |
| Sunday, September 30 |
| » Lost to Reds (91-63), 4-2 | Wrigley Field (39-38) | 60-94 | Lost 2 |
| » Starters: Hal Jeffcoat vs Bob Rush | Eighth | 33 out |
| Monday, October 1 |
| Future Cub Vance Law is born in Boise, ID. |
| Saturday, October 6 |
| Future Cub George Riley is born in Philadelphia, PA. |
| Monday, October 22 |
| Future Cub Frank DiPino is born in Syracuse, NY. |
| Monday, November 12 |
| Future Cub Jody Davis is born in Gainesville, GA. |
| Monday, November 19 |
| Future Cub Dickie Noles is born in Charlotte, NC. |
| Monday, December 24 |
| Former Cub Del Howard dies in Seattle, WA at the age of 80. |
Game information provided by Retrosheet (www.retrosheet.org) |