| Thursday, January 5 |
| Future Cub Henry Cotto is born in New York, NY. Former Cub Fred Luderus dies in Three Lakes, WI at the age of 76 |
| Tuesday, January 17 |
| Former Cub Bud Tinning dies in Evansville, IN at the age of 55. |
| Sunday, April 9 |
| Future Cub Brian Dorsett is born in Terre Haute, IN. |
| Tuesday, April 11 |
| » Lost to Reds (1-0), 7-1 | Crosley Field (0-1) | 0-1 | |
| » Starters: Glen Hobbie vs Jim O'Toole | Second | 1 out |
| Thursday, April 13 |
| » Lost to Reds (2-0), 5-2 | Crosley Field (0-2) | 0-2 | Lost 2 |
| » Starters: Dick Ellsworth vs Bob Purkey | Fifth | 2 out |
| Friday, April 14 |
| » Defeated Braves (1-2), 3-2 | Wrigley Field (1-0) | 1-2 | |
| » Starters: Bob Buhl vs Bob Anderson | Fourth | 2 out |
| Saturday, April 15 |
| » Defeated Braves (1-3), 9-5 | Wrigley Field (2-0) | 2-2 | Won 2 |
| » Starters: Carl Willey vs Glen Hobbie | Third | 1 out |
| Sunday, April 16 |
| » Major-league debuts: Ken Hunt (Reds) |
| Tuesday, April 18 |
| » Lost to Pirates (4-3), 5-3 | Forbes Field (0-1) | 2-3 | |
| » Starters: Dick Ellsworth vs Vinegar Bend Mizell | Fourth | 1½ out |
| Wednesday, April 19 |
| » Lost to Pirates (5-3), 4-1 | Forbes Field (0-2) | 2-4 | Lost 2 |
| » Starters: Bob Anderson vs Bob Friend | Fifth | 2½ out |
| Thursday, April 20 |
| » Defeated Pirates (5-4), 3-0 | Forbes Field (1-2) | 3-4 | |
| » Starters: Glen Hobbie vs Joe Gibbon | Fourth | 1½ out |
| Friday, April 21 |
| » Defeated Phillies (2-6), 3-2 | Shibe Park (1-0) | 4-4 | Won 2 |
| » Starters: Don Cardwell vs Robin Roberts | Third | ½ out |
| Saturday, April 22 |
| » Defeated Phillies (2-7), 6-4 | Shibe Park (2-0) | 5-4 | Won 3 |
| » Starters: Jack Curtis vs Chris Short | Second | 1½ out |
| » Major-league debuts: Jack Curtis (Cubs) |
| Sunday, April 23 |
| » Lost to Phillies (3-7), 1-0 | Shibe Park (2-1) | 5-5 | |
| » Starters: Dick Ellsworth vs Frank Sullivan | Fifth | 2 out |
| » Lost to Phillies (4-7), 6-0 | Shibe Park (2-2) | 5-6 | Lost 2 |
| » Starters: Bob Anderson vs Art Mahaffey | Fifth | 2 out |
| Tuesday, April 25 |
| » Major-league debuts: Fred Bruckbauer (Twins) |
| Wednesday, April 26 |
| » Defeated Reds (5-7), 3-2 | Wrigley Field (3-0) | 6-6 | |
| » Manager: Harry Craft |
| » Starters: Jim O'Toole vs Glen Hobbie | Fifth | 1½ out |
| Future Cub Curtis Wilkerson is born in Petersburg, VA. |
| Thursday, April 27 |
| » Defeated Reds (5-8), 5-2 | Wrigley Field (4-0) | 7-6 | Won 2 |
| » Starters: Ken Hunt vs Don Cardwell | Fourth | 1 out |
| Saturday, April 29 |
| » Lost to Dodgers (9-7), 9-4 | Wrigley Field (4-1) | 7-7 | |
| » Starters: Johnny Podres vs Dick Ellsworth | Fifth | 1½ out |
| Sunday, April 30 |
| » Lost to Dodgers (10-7), 2-1 | Wrigley Field (4-2) | 7-8 | Lost 2 |
| » Starters: Don Drysdale vs Glen Hobbie | Fifth | 2 out |
| » Defeated Dodgers (10-8), 10-5 | Wrigley Field (5-2) | 8-8 | |
| » Starters: Roger Craig vs Bob Anderson | Fifth | 2 out |
| Tuesday, May 2 |
| » Defeated Giants (10-7), 9-4 | Wrigley Field (6-2) | 9-8 | Won 2 |
| » Starters: Jack Sanford vs Don Cardwell | Fourth | 1½ out |
| Wednesday, May 3 |
| » Lost to Giants (11-7), 8-4 | Wrigley Field (6-3) | 9-9 | |
| » Starters: Mike McCormick vs Jack Curtis | Fifth | 2 out |
| Thursday, May 4 |
| » Lost to Giants (12-7), 9-3 | Wrigley Field (6-4) | 9-10 | Lost 2 |
| » Starters: Sam Jones vs Glen Hobbie | Sixth | 3 out |
| Saturday, May 6 |
| » Lost to Cardinals (9-10), 6-1 | Sportsman's Park III (0-1) | 9-11 | Lost 3 |
| » Starters: Jim Brewer vs Ray Sadecki | Seventh | 4 out |
| Sunday, May 7 |
| » Lost to Cardinals (10-10), 4-2 | Sportsman's Park III (0-2) | 9-12 | Lost 4 |
| » Starters: Don Cardwell vs Ernie Broglio | Seventh | 5 out |
| Tuesday, May 9 |
| » Lost to Braves (9-10), 8-5 | County Stadium (0-1) | 9-13 | Lost 5 |
| » Starters: Glen Hobbie vs Bob Buhl | Seventh | 5 out |
| Wednesday, May 10 |
| » Lost to Braves (10-10), 3-2 | County Stadium (0-2) | 9-14 | Lost 6 |
| » Starters: Dick Ellsworth vs Lew Burdette | Seventh | 6 out |
| Friday, May 12 |
| » Lost to Dodgers (17-11), 4-2 | Los Angeles Memorial Coliseum (0-1) | 9-15 | Lost 7 |
| » Manager: Vedie Himsl |
| » Starters: Don Cardwell vs Sandy Koufax | Seventh | 6 out |
| Saturday, May 13 |
| » Lost to Dodgers (18-11), 7-3 | Los Angeles Memorial Coliseum (0-2) | 9-16 | Lost 8 |
| » Starters: Bob Anderson vs Stan Williams | Seventh | 7 out |
| Sunday, May 14 |
| » Defeated Dodgers (18-12), 10-8 | Los Angeles Memorial Coliseum (1-2) | 10-16 | |
| » Starters: Glen Hobbie vs Don Drysdale | Seventh | 7 out |
| Monday, May 15 |
| » Lost to Giants (18-9), 14-1 | Candlestick Park (0-1) | 10-17 | |
| » Starters: Dick Ellsworth vs Mike McCormick | Seventh | 8 out |
| Tuesday, May 16 |
| » Lost to Giants (19-9), 2-1 | Candlestick Park (0-2) | 10-18 | Lost 2 |
| » Starters: Dick Drott vs Jack Sanford | Seventh | 9 out |
| Wednesday, May 17 |
| » Lost to Giants (20-9), 4-3 | Candlestick Park (0-3) | 10-19 | Lost 3 |
| » Starters: Don Cardwell vs Sam Jones | Seventh | 10 out |
| Friday, May 19 |
| » Defeated Cardinals (11-16), 1-0 | Wrigley Field (7-4) | 11-19 | |
| » Starters: Ray Sadecki vs Glen Hobbie | Seventh | 9 out |
| Saturday, May 20 |
| » Defeated Cardinals (11-17), 1-0 | Wrigley Field (8-4) | 12-19 | Won 2 |
| » Starters: Larry Jackson vs Dick Ellsworth | Seventh | 8 out |
| » Major-league debuts: Jimmie Schaffer (Cardinals) |
| Sunday, May 21 |
| » Lost to Cardinals (12-17), 6-3 | Wrigley Field (8-5) | 12-20 | |
| » Starters: Curt Simmons vs Don Cardwell | Seventh | 8½ out |
| » Lost to Cardinals (13-17), 3-0 | Wrigley Field (8-6) | 12-21 | Lost 2 |
| » Starters: Bob Gibson vs Dick Drott | Seventh | 8½ out |
| Tuesday, May 23 |
| » Lost to Phillies (10-23), 2-1 | Wrigley Field (8-7) | 12-22 | Lost 3 |
| » Starters: Frank Sullivan vs Glen Hobbie | Seventh | 9 out |
| Wednesday, May 24 |
| » Lost to Pirates (20-13), 7-3 | Wrigley Field (8-8) | 12-23 | Lost 4 |
| » Starters: Vinegar Bend Mizell vs Dick Ellsworth | Seventh | 10 out |
| Friday, May 26 |
| » Lost to Giants (23-13), 3-2 | Wrigley Field (8-9) | 12-24 | Lost 5 |
| » Starters: Juan Marichal vs Don Cardwell | Seventh | 11 out |
| Saturday, May 27 |
| » Lost to Giants (24-13), 8-2 | Wrigley Field (8-10) | 12-25 | Lost 6 |
| » Starters: Billy Loes vs Dick Drott | Seventh | 12 out |
| Sunday, May 28 |
| » Lost to Giants (25-13), 6-5 | Wrigley Field (8-11) | 12-26 | Lost 7 |
| » Starters: Jack Sanford vs Glen Hobbie | Seventh | 13 out |
| Tuesday, May 30 |
| » Defeated Pirates (20-17), 5-3 | Forbes Field (2-2) | 13-26 | |
| » Starters: Dick Ellsworth vs Vinegar Bend Mizell | Sixth | 10½ out |
| » Defeated Pirates (20-18), 10-0 | Forbes Field (3-2) | 14-26 | Won 2 |
| » Starters: Don Cardwell vs Bob Friend | Sixth | 10½ out |
| Wednesday, May 31 |
| » Defeated Phillies (12-27), 5-4 | Shibe Park (3-2) | 15-26 | Won 3 |
| » Manager: El Tappe |
| » Starters: Dick Drott vs Robin Roberts | Sixth | 10½ out |
| Thursday, June 1 |
| » Defeated Phillies (12-28), 10-3 | Shibe Park (4-2) | 16-26 | Won 4 |
| » Starters: Glen Hobbie vs Frank Sullivan | Seventh | 10 out |
| Friday, June 2 |
| » Defeated Reds (26-17), 7-6 | Crosley Field (1-2) | 17-26 | Won 5 |
| » Manager: Harry Craft |
| » Starters: Jack Curtis vs Bob Purkey | Seventh | 9 out |
| Saturday, June 3 |
| » Defeated Reds (26-18), 10-7 | Crosley Field (2-2) | 18-26 | Won 6 |
| » Starters: Dick Ellsworth vs Ken Hunt | Seventh | 9 out |
| Sunday, June 4 |
| » Lost to Reds (27-18), 3-1 | Crosley Field (2-3) | 18-27 | |
| » Starters: Bob Anderson vs Jim Maloney | Sixth | 8½ out |
| » Defeated Reds (27-19), 8-2 | Crosley Field (3-3) | 19-27 | |
| » Starters: Don Cardwell vs Jim O'Toole | Sixth | 8½ out |
| Monday, June 5 |
| » Lost to Cardinals (21-24), 10-8 | Sportsman's Park III (0-3) | 19-28 | |
| » Manager: Vedie Himsl |
| » Starters: Dick Ellsworth vs Curt Simmons | Seventh | 9 out |
| Tuesday, June 6 |
| » Lost to Cardinals (22-24), 6-2 | Sportsman's Park III (0-4) | 19-29 | Lost 2 |
| » Starters: Glen Hobbie vs Ernie Broglio | Seventh | 10 out |
| » Tied Cardinals, 3-3 | Sportsman's Park III (0-4) | 19-29 | |
| » Starters: Jack Curtis vs Ray Sadecki | Seventh | 10 out |
| Wednesday, June 7 |
| » Lost to Cardinals (23-24), 8-6 | Sportsman's Park III (0-5) | 19-30 | Lost 3 |
| » Starters: Bob Anderson vs Larry Jackson | Seventh | 10½ out |
| Friday, June 9 |
| » Defeated Braves (22-26), 11-10 | Wrigley Field (9-11) | 20-30 | |
| » Manager: El Tappe |
| » Starters: Bob Buhl vs Don Cardwell | Seventh | 10 out |
| Future Cub Tom Edens is born in Ontario, OR. |
| Saturday, June 10 |
| » Lost to Braves (23-26), 9-5 | Wrigley Field (9-12) | 20-31 | |
| » Starters: Lew Burdette vs Glen Hobbie | Seventh | 11 out |
| Sunday, June 11 |
| » Lost to Braves (24-26), 8-4 | Wrigley Field (9-13) | 20-32 | Lost 2 |
| » Starters: Carl Willey vs Dick Ellsworth | Sixth | 11½ out |
| » Defeated Braves (24-27), 5-3 | Wrigley Field (10-13) | 21-32 | |
| » Starters: Don Nottebart vs Jack Curtis | Sixth | 11½ out |
| Monday, June 12 |
| » Major-league debuts: Jerry Arrigo (Twins) |
| Wednesday, June 14 |
| » Lost to Dodgers (35-24), 7-0 | Los Angeles Memorial Coliseum (1-3) | 21-33 | |
| » Starters: Don Cardwell vs Don Drysdale | Fifth | 11½ out |
| Thursday, June 15 |
| » Lost to Dodgers (36-24), 6-3 | Los Angeles Memorial Coliseum (1-4) | 21-34 | Lost 2 |
| » Starters: Glen Hobbie vs Johnny Podres | Sixth | 12½ out |
| Friday, June 16 |
| » Defeated Giants (34-24), 12-6 | Candlestick Park (1-3) | 22-34 | |
| » Starters: Dick Ellsworth vs Billy Loes | Seventh | 12 out |
| Saturday, June 17 |
| » Lost to Giants (35-24), 9-3 | Candlestick Park (1-4) | 22-35 | |
| » Starters: Jack Curtis vs Billy O'Dell | Seventh | 13 out |
| Sunday, June 18 |
| » Lost to Giants (36-24), 7-2 | Candlestick Park (1-5) | 22-36 | Lost 2 |
| » Starters: Don Cardwell vs Juan Marichal | Seventh | 14½ out |
| Tuesday, June 20 |
| » Lost to Dodgers (38-26), 3-0 | Wrigley Field (10-14) | 22-37 | Lost 3 |
| » Starters: Sandy Koufax vs Glen Hobbie | Seventh | 15 out |
| Future Cub Gary Varsho is born in Marshfield, WI. |
| Wednesday, June 21 |
| » Lost to Dodgers (39-26), 4-1 | Wrigley Field (10-15) | 22-38 | Lost 4 |
| » Starters: Stan Williams vs Dick Ellsworth | Seventh | 16½ out |
| » Lost to Dodgers (40-26), 4-2 | Wrigley Field (10-16) | 22-39 | Lost 5 |
| » Starters: Johnny Podres vs Don Cardwell | Seventh | 16½ out |
| Thursday, June 22 |
| » Defeated Dodgers (40-27), 7-5 | Wrigley Field (11-16) | 23-39 | |
| » Starters: Roger Craig vs Dick Drott | Seventh | 16½ out |
| Friday, June 23 |
| » Defeated Braves (29-31), 5-3 | County Stadium (1-2) | 24-39 | Won 2 |
| » Starters: Jack Curtis vs Bob Hendley | Seventh | 16½ out |
| » Major-league debuts: Bob Hendley (Braves) |
| Saturday, June 24 |
| » Lost to Braves (30-31), 13-4 | County Stadium (1-3) | 24-40 | |
| » Starters: Glen Hobbie vs Tony Cloninger | Seventh | 16½ out |
| Sunday, June 25 |
| » Defeated Braves (30-32), 5-3 | County Stadium (2-3) | 25-40 | |
| » Starters: Don Cardwell vs Warren Spahn | Seventh | 16½ out |
| Monday, June 26 |
| Former Cub Bill Collins dies in San Bernardino, CA at the age of 80. |
| Tuesday, June 27 |
| » Lost to Reds (44-25), 10-8 | Wrigley Field (11-17) | 25-41 | |
| » Starters: Ken Hunt vs Dick Ellsworth | Seventh | 17½ out |
| » Major-league debuts: Johnny Edwards (Reds) |
| Wednesday, June 28 |
| » Defeated Reds (44-26), 16-5 | Wrigley Field (12-17) | 26-41 | |
| » Starters: Bob Purkey vs Glen Hobbie | Seventh | 15½ out |
| » Defeated Reds (44-27), 7-2 | Wrigley Field (13-17) | 27-41 | Won 2 |
| » Starters: Jim O'Toole vs Jack Curtis | Seventh | 15½ out |
| Thursday, June 29 |
| » Defeated Reds (44-28), 15-8 | Wrigley Field (14-17) | 28-41 | Won 3 |
| » Starters: Jim Maloney vs Don Cardwell | Seventh | 14½ out |
| Friday, June 30 |
| » Lost to Cardinals (31-38), 11-4 | Wrigley Field (14-18) | 28-42 | |
| » Starters: Ray Sadecki vs Jim Brewer | Seventh | 15½ out |
| » Major-league debuts: Jerry Buchek (Cardinals) |
| Saturday, July 1 |
| » Defeated Cardinals (31-39), 13-1 | Wrigley Field (15-18) | 29-42 | |
| » Starters: Bob Miller vs Dick Ellsworth | Seventh | 14½ out |
| Sunday, July 2 |
| » Defeated Cardinals (31-40), 10-9 | Wrigley Field (16-18) | 30-42 | Won 2 |
| » Starters: Al Cicotte vs Glen Hobbie | Seventh | 15 out |
| Tuesday, July 4 |
| » Lost to Giants (43-33), 19-3 | Wrigley Field (16-19) | 30-43 | |
| » Starters: Eddie Fisher vs Don Cardwell | Seventh | 16 out |
| » Defeated Giants (43-34), 3-2 | Wrigley Field (17-19) | 31-43 | |
| » Starters: Billy Loes vs Jack Curtis | Seventh | 16 out |
| Thursday, July 6 |
| » Lost to Pirates (39-34), 15-3 | Wrigley Field (17-20) | 31-44 | |
| » Starters: Bob Friend vs Dick Ellsworth | Seventh | 17 out |
| » Defeated Pirates (39-35), 5-1 | Wrigley Field (18-20) | 32-44 | |
| » Starters: Vinegar Bend Mizell vs Glen Hobbie | Seventh | 17 out |
| Friday, July 7 |
| » Defeated Phillies (23-52), 9-3 | Wrigley Field (19-20) | 33-44 | Won 2 |
| » Starters: Chris Short vs Don Cardwell | Seventh | 17½ out |
| Saturday, July 8 |
| » Defeated Phillies (23-53), 6-4 | Wrigley Field (20-20) | 34-44 | Won 3 |
| » Starters: Jim Owens vs Jack Curtis | Seventh | 16½ out |
| Sunday, July 9 |
| » Defeated Phillies (23-54), 9-8 | Wrigley Field (21-20) | 35-44 | Won 4 |
| » Starters: Art Mahaffey vs Glen Hobbie | Seventh | 16 out |
| » Defeated Phillies (23-55), 8-5 | Wrigley Field (22-20) | 36-44 | Won 5 |
| » Starters: Frank Sullivan vs Jim Brewer | Seventh | 16 out |
| Thursday, July 13 |
| » Lost to Reds (55-30), 4-3 | Crosley Field (3-4) | 36-45 | |
| » Starters: Don Cardwell vs Jim O'Toole | Seventh | 17 out |
| Friday, July 14 |
| » Defeated Reds (55-31), 8-7 | Crosley Field (4-4) | 37-45 | |
| » Starters: Glen Hobbie vs Bob Purkey | Seventh | 16 out |
| Saturday, July 15 |
| » Lost to Reds (56-31), 2-1 | Crosley Field (4-5) | 37-46 | |
| » Starters: Jack Curtis vs Joey Jay | Seventh | 17 out |
| Sunday, July 16 |
| » Defeated Reds (56-32), 4-2 | Crosley Field (5-5) | 38-46 | |
| » Starters: Dick Ellsworth vs Ken Hunt | Seventh | 16 out |
| Former Cub Mike Mitchell dies in Phoenix, AZ at the age of 82. |
| Monday, July 17 |
| » Lost to Cardinals (39-45), 10-6 | Sportsman's Park III (0-6) | 38-47 | |
| » Starters: Don Cardwell vs Curt Simmons | Seventh | 16½ out |
| » Lost to Cardinals (40-45), 8-5 | Sportsman's Park III (0-7) | 38-48 | Lost 2 |
| » Starters: Jim Brewer vs Ernie Broglio | Seventh | 16½ out |
| Former Cub Ed Reulbach dies in Glens Falls, NY at the age of 79. |
| Tuesday, July 18 |
| » Lost to Cardinals (41-45), 8-3 | Sportsman's Park III (0-8) | 38-49 | Lost 3 |
| » Starters: Glen Hobbie vs Larry Jackson | Seventh | 17 out |
| » Lost to Cardinals (42-45), 7-5 | Sportsman's Park III (0-9) | 38-50 | Lost 4 |
| » Starters: Dick Drott vs Bob Gibson | Seventh | 17 out |
| Thursday, July 20 |
| » Lost to Pirates (44-39), 4-0 | Forbes Field (3-3) | 38-51 | Lost 5 |
| » Starters: Jack Curtis vs Joe Gibbon | Seventh | 16½ out |
| Friday, July 21 |
| » Lost to Phillies (28-59), 4-3 | Shibe Park (4-3) | 38-52 | Lost 6 |
| » Starters: Don Cardwell vs Jim Owens | Seventh | 17 out |
| Saturday, July 22 |
| » Lost to Phillies (29-59), 6-5 | Shibe Park (4-4) | 38-53 | Lost 7 |
| » Starters: Glen Hobbie vs Chris Short | Seventh | 17 out |
| Sunday, July 23 |
| » Defeated Phillies (29-60), 11-5 | Shibe Park (5-4) | 39-53 | |
| » Starters: Jim Brewer vs Art Mahaffey | Seventh | 17½ out |
| » Major-league debuts: Paul Brown (Phillies) |
| Future Cub Chuck Crim is born in Van Nuys, CA. |
| Tuesday, July 25 |
| » Lost to Cardinals (45-48), 6-5 | Wrigley Field (22-21) | 39-54 | |
| » Starters: Ray Sadecki vs Jack Curtis | Seventh | 18 out |
| Wednesday, July 26 |
| » Defeated Cardinals (45-49), 7-6 | Wrigley Field (23-21) | 40-54 | |
| » Starters: Curt Simmons vs Don Cardwell | Seventh | 18 out |
| Thursday, July 27 |
| » Defeated Cardinals (45-50), 3-2 | Wrigley Field (24-21) | 41-54 | Won 2 |
| » Starters: Al Cicotte vs Glen Hobbie | Seventh | 18 out |
| Friday, July 28 |
| » Lost to Reds (62-38), 4-3 | Wrigley Field (24-22) | 41-55 | |
| » Starters: Jim O'Toole vs Dick Ellsworth | Seventh | 19 out |
| Saturday, July 29 |
| » Defeated Reds (62-39), 7-6 | Wrigley Field (25-22) | 42-55 | |
| » Starters: Joey Jay vs Jack Curtis | Seventh | 18 out |
| Sunday, July 30 |
| » Defeated Reds (62-40), 3-2 | Wrigley Field (26-22) | 43-55 | Won 2 |
| » Starters: Ken Hunt vs Don Cardwell | Seventh | 18½ out |
| » Lost to Reds (63-40), 5-4 | Wrigley Field (26-23) | 43-56 | |
| » Starters: Ken Johnson vs Jim Brewer | Seventh | 18½ out |
| Wednesday, August 2 |
| » Lost to Braves (51-48), 4-2 | Wrigley Field (26-24) | 43-57 | Lost 2 |
| » Starters: Carl Willey vs Glen Hobbie | Seventh | 19½ out |
| » Tied Braves, 7-7 | Wrigley Field (26-24) | 43-57 | |
| » Starters: Bob Buhl vs Jack Curtis | Seventh | 19½ out |
| Thursday, August 3 |
| » Lost to Braves (52-48), 5-2 | Wrigley Field (26-25) | 43-58 | Lost 3 |
| » Starters: Lew Burdette vs Don Cardwell | Seventh | 20½ out |
| Former Cub Tom Downey dies in Passaic, NJ at the age of 78. |
| Friday, August 4 |
| » Defeated Dodgers (63-40), 4-2 | Los Angeles Memorial Coliseum (2-4) | 44-58 | |
| » Starters: Bob Anderson vs Sandy Koufax | Seventh | 20½ out |
| Saturday, August 5 |
| » Lost to Dodgers (64-40), 7-6 | Los Angeles Memorial Coliseum (2-5) | 44-59 | |
| » Starters: Jim Brewer vs Don Drysdale | Seventh | 20½ out |
| Sunday, August 6 |
| » Lost to Dodgers (65-40), 11-4 | Los Angeles Memorial Coliseum (2-6) | 44-60 | Lost 2 |
| » Starters: Jack Curtis vs Johnny Podres | Seventh | 20½ out |
| Tuesday, August 8 |
| » Lost to Giants (57-49), 8-1 | Candlestick Park (1-6) | 44-61 | Lost 3 |
| » Starters: Don Cardwell vs Jack Sanford | Seventh | 21½ out |
| Wednesday, August 9 |
| » Lost to Giants (58-49), 6-5 | Candlestick Park (1-7) | 44-62 | Lost 4 |
| » Starters: Bob Anderson vs Mike McCormick | Seventh | 22½ out |
| Friday, August 11 |
| » Lost to Braves (55-51), 2-1 | County Stadium (2-4) | 44-63 | Lost 5 |
| » Starters: Jack Curtis vs Warren Spahn | Seventh | 23 out |
| Saturday, August 12 |
| » Lost to Braves (56-51), 8-6 | County Stadium (2-5) | 44-64 | Lost 6 |
| » Starters: Don Cardwell vs Bob Hendley | Seventh | 24 out |
| Sunday, August 13 |
| » Lost to Braves (57-51), 8-3 | County Stadium (2-6) | 44-65 | Lost 7 |
| » Starters: Bob Anderson vs Lew Burdette | Seventh | 25 out |
| Monday, August 14 |
| » Defeated Phillies (30-81), 9-2 | Wrigley Field (27-25) | 45-65 | |
| » Starters: Frank Sullivan vs Dick Ellsworth | Seventh | 24 out |
| Tuesday, August 15 |
| » Defeated Phillies (30-82), 6-5 | Wrigley Field (28-25) | 46-65 | Won 2 |
| » Starters: Art Mahaffey vs Jack Curtis | Seventh | 23 out |
| Wednesday, August 16 |
| » Defeated Phillies (30-83), 9-5 | Wrigley Field (29-25) | 47-65 | Won 3 |
| » Starters: Chris Short vs Don Cardwell | Seventh | 22½ out |
| Thursday, August 17 |
| » Defeated Pirates (54-57), 11-4 | Wrigley Field (30-25) | 48-65 | Won 4 |
| » Starters: Vinegar Bend Mizell vs Glen Hobbie | Seventh | 22½ out |
| » Lost to Pirates (55-57), 4-3 | Wrigley Field (30-26) | 48-66 | |
| » Starters: Earl Francis vs Jim Brewer | Seventh | 22½ out |
| Friday, August 18 |
| » Defeated Pirates (55-58), 2-1 | Wrigley Field (31-26) | 49-66 | |
| » Starters: Tom Sturdivant vs Dick Ellsworth | Seventh | 22½ out |
| Saturday, August 19 |
| » Lost to Pirates (56-58), 4-3 | Wrigley Field (31-27) | 49-67 | |
| » Starters: Harvey Haddix vs Jack Curtis | Seventh | 23½ out |
| Sunday, August 20 |
| » Defeated Pirates (56-59), 1-0 | Wrigley Field (32-27) | 50-67 | |
| » Starters: Bob Friend vs Don Cardwell | Seventh | 22½ out |
| Tuesday, August 22 |
| » Lost to Phillies (32-87), 6-0 | Shibe Park (5-5) | 50-68 | |
| » Starters: Dick Ellsworth vs Art Mahaffey | Seventh | 22 out |
| Thursday, August 24 |
| » Lost to Phillies (33-87), 7-4 | Shibe Park (5-6) | 50-69 | Lost 2 |
| » Starters: Jack Curtis vs Jim Owens | Seventh | 22½ out |
| Friday, August 25 |
| » Lost to Pirates (59-60), 1-0 | Forbes Field (3-4) | 50-70 | Lost 3 |
| » Starters: Don Cardwell vs Tom Sturdivant | Seventh | 22½ out |
| Saturday, August 26 |
| » Defeated Pirates (59-61), 7-3 | Forbes Field (4-4) | 51-70 | |
| » Starters: Dick Ellsworth vs Harvey Haddix | Seventh | 21½ out |
| Sunday, August 27 |
| » Lost to Pirates (60-61), 7-3 | Forbes Field (4-5) | 51-71 | |
| » Starters: Jack Curtis vs Joe Gibbon | Seventh | 22½ out |
| » Defeated Pirates (60-62), 6-5 | Forbes Field (5-5) | 52-71 | |
| » Starters: Jim Brewer vs Vinegar Bend Mizell | Seventh | 22½ out |
| Monday, August 28 |
| » Defeated Pirates (60-63), 5-4 | Forbes Field (6-5) | 53-71 | Won 2 |
| » Starters: Dick Drott vs Earl Francis | Seventh | 22 out |
| Tuesday, August 29 |
| » Lost to Dodgers (72-52), 2-1 | Wrigley Field (32-28) | 53-72 | |
| » Starters: Sandy Koufax vs Don Cardwell | Seventh | 23 out |
| Wednesday, August 30 |
| » Lost to Dodgers (73-52), 5-2 | Wrigley Field (32-29) | 53-73 | Lost 2 |
| » Starters: Johnny Podres vs Dick Ellsworth | Seventh | 23 out |
| Thursday, August 31 |
| » Defeated Giants (69-57), 6-1 | Wrigley Field (33-29) | 54-73 | |
| » Starters: Juan Marichal vs Jack Curtis | Seventh | 22½ out |
| Friday, September 1 |
| » Lost to Giants (70-57), 4-3 | Wrigley Field (33-30) | 54-74 | |
| » Manager: Lou Klein |
| » Starters: Dick LeMay vs Glen Hobbie | Seventh | 23 out |
| Saturday, September 2 |
| » Defeated Giants (70-58), 7-0 | Wrigley Field (34-30) | 55-74 | |
| » Starters: Jack Sanford vs Don Cardwell | Seventh | 23 out |
| Sunday, September 3 |
| » Defeated Braves (71-59), 6-5 | Wrigley Field (35-30) | 56-74 | Won 2 |
| » Starters: Lew Burdette vs Jim Brewer | Seventh | 22½ out |
| » Lost to Braves (72-59), 4-2 | Wrigley Field (35-31) | 56-75 | |
| » Starters: Tony Cloninger vs Dick Ellsworth | Seventh | 22½ out |
| Monday, September 4 |
| » Defeated Braves (72-60), 6-2 | Wrigley Field (36-31) | 57-75 | |
| » Starters: Carl Willey vs Jack Curtis | Seventh | 22 out |
| Tuesday, September 5 |
| » Lost to Pirates (64-66), 8-3 | Wrigley Field (36-32) | 57-76 | |
| » Starters: Tom Sturdivant vs Glen Hobbie | Seventh | 23 out |
| Wednesday, September 6 |
| » Defeated Pirates (64-67), 6-2 | Wrigley Field (37-32) | 58-76 | |
| » Starters: Joe Gibbon vs Don Cardwell | Seventh | 22 out |
| Thursday, September 7 |
| » Lost to Pirates (65-67), 7-5 | Wrigley Field (37-33) | 58-77 | |
| » Starters: Harvey Haddix vs Jim Brewer | Seventh | 22½ out |
| Friday, September 8 |
| » Defeated Phillies (39-97), 4-1 | Wrigley Field (38-33) | 59-77 | |
| » Starters: Art Mahaffey vs Dick Ellsworth | Seventh | 22½ out |
| Saturday, September 9 |
| » Lost to Phillies (40-97), 6-2 | Wrigley Field (38-34) | 59-78 | |
| » Starters: Jim Owens vs Jack Curtis | Seventh | 23½ out |
| Sunday, September 10 |
| » Lost to Phillies (41-97), 14-6 | Wrigley Field (38-35) | 59-79 | Lost 2 |
| » Starters: Robin Roberts vs Don Cardwell | Seventh | 24½ out |
| » Major-league debuts: Lou Brock and Ken Hubbs (Cubs) |
| Monday, September 11 |
| » Major-league debuts: Dean Chance (Angels) |
| Tuesday, September 12 |
| » Lost to Reds (86-56), 7-2 | Crosley Field (5-6) | 59-80 | Lost 3 |
| » Manager: El Tappe |
| » Starters: Dick Ellsworth vs Jim O'Toole | Seventh | 25½ out |
| Thursday, September 14 |
| » Lost to Cardinals (73-67), 8-7 | Sportsman's Park III (0-10) | 59-81 | Lost 4 |
| » Starters: Don Cardwell vs Ernie Broglio | Seventh | 27 out |
| » Lost to Cardinals (74-67), 6-5 | Sportsman's Park III (0-11) | 59-82 | Lost 5 |
| » Starters: Jack Curtis vs Curt Simmons | Seventh | 27 out |
| Friday, September 15 |
| » Lost to Giants (76-64), 5-1 | Candlestick Park (1-8) | 59-83 | Lost 6 |
| » Starters: Dick Drott vs Jack Sanford | Seventh | 27½ out |
| Saturday, September 16 |
| » Lost to Giants (77-64), 4-3 | Candlestick Park (1-9) | 59-84 | Lost 7 |
| » Starters: Dick Ellsworth vs Mike McCormick | Seventh | 28½ out |
| Future Cub Mark Parent is born in Ashland, OR. |
| Sunday, September 17 |
| » Lost to Giants (78-64), 8-2 | Candlestick Park (1-10) | 59-85 | Lost 8 |
| » Starters: Jack Curtis vs Billy O'Dell | Sixth | 28½ out |
| Monday, September 18 |
| » Defeated Dodgers (83-60), 5-3 | Los Angeles Memorial Coliseum (3-6) | 60-85 | |
| » Starters: Don Cardwell vs Phil Ortega | Sixth | 28 out |
| Tuesday, September 19 |
| » Defeated Dodgers (83-61), 7-3 | Los Angeles Memorial Coliseum (4-6) | 61-85 | Won 2 |
| » Starters: Bob Anderson vs Stan Williams | Seventh | 28 out |
| Wednesday, September 20 |
| » Lost to Dodgers (84-61), 3-2 | Los Angeles Memorial Coliseum (4-7) | 61-86 | |
| » Starters: Dick Ellsworth vs Sandy Koufax | Sixth | 29 out |
| Saturday, September 23 |
| » Lost to Braves (78-69), 6-3 | County Stadium (2-7) | 61-87 | Lost 2 |
| » Starters: Jack Curtis vs Tony Cloninger | Seventh | 29½ out |
| Sunday, September 24 |
| » Lost to Braves (79-69), 8-0 | County Stadium (2-8) | 61-88 | Lost 3 |
| » Starters: Don Cardwell vs Warren Spahn | Seventh | 29 out |
| » Defeated Braves (79-70), 4-2 | County Stadium (3-8) | 62-88 | |
| » Starters: Dick Ellsworth vs Bob Hendley | Seventh | 29 out |
| Tuesday, September 26 |
| » Lost to Reds (92-59), 6-3 | Wrigley Field (38-36) | 62-89 | |
| » Starters: Bob Purkey vs Bob Anderson | Seventh | 30 out |
| Future Cub Steve Buechele is born in Lancaster, CA. |
| Wednesday, September 27 |
| » Defeated Cardinals (78-74), 5-2 | Wrigley Field (39-36) | 63-89 | |
| » Starters: Larry Jackson vs Don Cardwell | Seventh | 29½ |
