| Friday, January 5 |
| Future Cub Danny Jackson is born in San Antonio, TX. |
| Thursday, January 11 |
| Future Cub Donn Pall is born in Chicago, IL. |
| Friday, January 19 |
| Future Cub Chris Sabo is born in Detroit, MI. |
| Friday, February 2 |
| Future Cub Paul Kilgus is born in Bowling Green, KY. |
| Sunday, February 4 |
| Future Cub Dan Plesac is born in Gary, IN. |
| Saturday, February 10 |
| Former Cub Roy Walker dies in New Orleans, LA at the age of 69. |
| Thursday, February 15 |
| Future Cub Rolando Roomes is born in Kingston, Jamaica. |
| Sunday, March 25 |
| Future Cub Jeff Kunkel is born in West Palm Beach, FL. |
| Tuesday, April 10 |
| » Lost to Astros (1-0), 11-2 | Colt Stadium (0-1) | 0-1 | |
| » Starters: Don Cardwell vs Bobby Shantz | Fourth | 1 out |
| Wednesday, April 11 |
| » Lost to Astros (2-0), 2-0 | Colt Stadium (0-2) | 0-2 | Lost 2 |
| » Starters: Glen Hobbie vs Hal Woodeshick | Sixth | 2 out |
| Thursday, April 12 |
| » Lost to Astros (3-0), 2-0 | Colt Stadium (0-3) | 0-3 | Lost 3 |
| » Starters: Jack Curtis vs Dean Stone | Seventh | 3 out |
| Friday, April 13 |
| » Lost to Cardinals (2-0), 8-5 | Wrigley Field (0-1) | 0-4 | Lost 4 |
| » Starters: Ray Washburn vs Dick Ellsworth | Seventh | 4 out |
| » Major-league debuts: Morrie Steevens (Cubs) |
| Saturday, April 14 |
| » Lost to Cardinals (3-0), 7-4 | Wrigley Field (0-2) | 0-5 | Lost 5 |
| » Starters: Curt Simmons vs Don Cardwell | Eighth | 5 out |
| » Major-league debuts: Cal Koonce (Cubs) |
| Sunday, April 15 |
| » Major-league debuts: Dick Phillips (Giants) |
| Monday, April 16 |
| » Lost to Pirates (5-0), 6-5 | Wrigley Field (0-3) | 0-6 | Lost 6 |
| » Starters: Bob Veale vs Glen Hobbie | Ninth | 5½ out |
| » Major-league debuts: Bob Veale (Pirates) |
| Tuesday, April 17 |
| » Lost to Pirates (6-0), 10-6 | Wrigley Field (0-4) | 0-7 | Lost 7 |
| » Starters: Tom Sturdivant vs Jack Curtis | Tenth | 6½ out |
| » Major-league debuts: Jack Lamabe (Pirates) |
| Wednesday, April 18 |
| » Defeated Astros (4-3), 3-2 | Wrigley Field (1-4) | 1-7 | |
| » Starters: Hal Woodeshick vs Dick Ellsworth | Ninth | 6½ out |
| Thursday, April 19 |
| » Lost to Astros (5-3), 6-0 | Wrigley Field (1-5) | 1-8 | |
| » Starters: Dean Stone vs Don Cardwell | Ninth | 7½ out |
| Saturday, April 21 |
| » Lost to Cardinals (7-0), 8-0 | Sportsman's Park III (0-1) | 1-9 | Lost 2 |
| » Starters: Glen Hobbie vs Curt Simmons | Ninth | 8½ out |
| Future Cub Les Lancaster is born in Dallas, TX. |
| Sunday, April 22 |
| » Defeated Cardinals (7-1), 11-5 | Sportsman's Park III (1-1) | 2-9 | |
| » Starters: Dick Ellsworth vs Ray Sadecki | Ninth | 8 out |
| » Defeated Cardinals (7-2), 5-1 | Sportsman's Park III (2-1) | 3-9 | Won 2 |
| » Starters: Cal Koonce vs Bob Gibson | Ninth | 8 out |
| » Major-league debuts: Paul Toth (Cardinals) |
| Tuesday, April 24 |
| » Lost to Dodgers (9-5), 10-2 | Wrigley Field (1-6) | 3-10 | |
| » Starters: Sandy Koufax vs Don Cardwell | Eighth | 8½ out |
| Wednesday, April 25 |
| » Defeated Dodgers (9-6), 9-6 | Wrigley Field (2-6) | 4-10 | |
| » Starters: Johnny Podres vs Glen Hobbie | Ninth | 7½ out |
| Thursday, April 26 |
| » Lost to Dodgers (10-6), 12-5 | Wrigley Field (2-7) | 4-11 | |
| » Starters: Pete Richert vs Dick Ellsworth | Ninth | 8 out |
| Friday, April 27 |
| » Lost to Giants (11-5), 5-4 | Candlestick Park (0-1) | 4-12 | Lost 2 |
| » Starters: Cal Koonce vs Billy O'Dell | Seventh | 8 out |
| Saturday, April 28 |
| » Lost to Giants (12-5), 11-2 | Candlestick Park (0-2) | 4-13 | Lost 3 |
| » Starters: Al Lary vs Juan Marichal | Eighth | 8 out |
| Future Cub Luis Quinones is born in Ponce, P.R. |
| Sunday, April 29 |
| » Lost to Giants (13-5), 7-0 | Candlestick Park (0-3) | 4-14 | Lost 4 |
| » Starters: Glen Hobbie vs Jack Sanford | Ninth | 10 out |
| » Lost to Giants (14-5), 6-0 | Candlestick Park (0-4) | 4-15 | Lost 5 |
| » Starters: Jack Curtis vs Billy Pierce | Ninth | 10 out |
| Monday, April 30 |
| » Lost to Dodgers (13-8), 3-1 | Dodger Stadium (0-1) | 4-16 | Lost 6 |
| » Starters: Dick Ellsworth vs Stan Williams | Eighth | 11 out |
| Former Cub Al Demaree dies in Los Angeles, CA at the age of 78. |
| Tuesday, May 1 |
| » Lost to Dodgers (14-8), 6-5 | Dodger Stadium (0-2) | 4-17 | Lost 7 |
| » Manager: Lou Klein |
| » Starters: Cal Koonce vs Don Drysdale | Ninth | 12 out |
| Wednesday, May 2 |
| » Defeated Dodgers (14-9), 3-1 | Dodger Stadium (1-2) | 5-17 | |
| » Starters: Bob Buhl vs Sandy Koufax | Ninth | 12 out |
| Friday, May 4 |
| » Lost to Giants (19-5), 11-6 | Wrigley Field (2-8) | 5-18 | |
| » Starters: Billy Pierce vs Dick Ellsworth | Ninth | 13½ out |
| » Major-league debuts: Daryl Robertson (Cubs) |
| Saturday, May 5 |
| » Defeated Giants (19-6), 12-8 | Wrigley Field (3-8) | 6-18 | |
| » Starters: Gaylord Perry vs Cal Koonce | Ninth | 12½ out |
| Sunday, May 6 |
| » Lost to Giants (20-6), 7-3 | Wrigley Field (3-9) | 6-19 | |
| » Starters: Billy O'Dell vs Bob Buhl | Ninth | 13½ out |
| Tuesday, May 8 |
| » Lost to Mets (5-16), 3-1 | Wrigley Field (3-10) | 6-20 | Lost 2 |
| » Starters: Jay Hook vs Don Cardwell | Ninth | 14½ out |
| Friday, May 11 |
| » Lost to Phillies (13-11), 12-2 | Wrigley Field (3-11) | 6-21 | Lost 3 |
| » Starters: Jack Hamilton vs Dick Ellsworth | Tenth | 14½ out |
| Saturday, May 12 |
| » Defeated Phillies (13-12), 9-8 | Wrigley Field (4-11) | 7-21 | |
| » Starters: Cal McLish vs Cal Koonce | Tenth | 14½ out |
| » Major-league debuts: Dennis Bennett (Phillies) |
| Sunday, May 13 |
| » Defeated Phillies (13-13), 8-7 | Wrigley Field (5-11) | 8-21 | Won 2 |
| » Starters: Jim Owens vs Don Cardwell | Ninth | 14 out |
| » Defeated Phillies (13-14), 8-5 | Wrigley Field (6-11) | 9-21 | Won 3 |
| » Starters: Chris Short vs Jim Brewer | Ninth | 14 out |
| Tuesday, May 15 |
| » Lost to Mets (8-18), 6-5 | Polo Grounds V (0-1) | 9-22 | |
| » Starters: Bob Buhl vs Vinegar Bend Mizell | Tenth | 15 out |
| Wednesday, May 16 |
| » Lost to Mets (9-18), 6-5 | Polo Grounds V (0-2) | 9-23 | Lost 2 |
| » Starters: Dick Ellsworth vs Al Jackson | Tenth | 16 out |
| Friday, May 18 |
| » Defeated Phillies (14-17), 11-8 | Shibe Park (1-0) | 10-23 | |
| » Starters: Don Cardwell vs Dennis Bennett | Tenth | 14½ out |
| Saturday, May 19 |
| » Lost to Phillies (15-17), 7-5 | Shibe Park (1-1) | 10-24 | |
| » Starters: Glen Hobbie vs Art Mahaffey | Tenth | 15½ out |
| Sunday, May 20 |
| » Defeated Phillies (15-18), 6-4 | Shibe Park (2-1) | 11-24 | |
| » Starters: Cal Koonce vs Jim Owens | Tenth | 14½ out |
| » Defeated Phillies (15-19), 11-2 | Shibe Park (3-1) | 12-24 | Won 2 |
| » Starters: Bob Buhl vs Jack Hamilton | Tenth | 14½ out |
| Monday, May 21 |
| » Lost to Pirates (18-16), 8-4 | Forbes Field (0-1) | 12-25 | |
| » Starters: Dick Ellsworth vs Earl Francis | Tenth | 14½ out |
| Tuesday, May 22 |
| » Defeated Pirates (18-17), 3-1 | Forbes Field (1-1) | 13-25 | |
| » Starters: Don Cardwell vs Bob Friend | Tenth | 13½ out |
| Wednesday, May 23 |
| » Lost to Braves (17-22), 4-2 | County Stadium (0-1) | 13-26 | |
| » Starters: Glen Hobbie vs Warren Spahn | Tenth | 13½ out |
| Thursday, May 24 |
| » Defeated Braves (17-23), 4-3 | County Stadium (1-1) | 14-26 | |
| » Starters: Bob Buhl vs Bob Hendley | Ninth | 13½ out |
| Friday, May 25 |
| » Lost to Reds (22-16), 2-1 | Crosley Field (0-1) | 14-27 | |
| » Starters: Cal Koonce vs Moe Drabowsky | Ninth | 14½ out |
| Saturday, May 26 |
| » Lost to Reds (23-16), 11-6 | Crosley Field (0-2) | 14-28 | Lost 2 |
| » Starters: Dick Ellsworth vs Jim O'Toole | Ninth | 15½ out |
| Sunday, May 27 |
| » Lost to Reds (24-16), 10-0 | Crosley Field (0-3) | 14-29 | Lost 3 |
| » Starters: Don Cardwell vs Bob Purkey | Ninth | 17 out |
| Monday, May 28 |
| » Defeated Braves (19-25), 2-1 | Wrigley Field (7-11) | 15-29 | |
| » Starters: Warren Spahn vs Glen Hobbie | Ninth | 16½ out |
| Tuesday, May 29 |
| » Lost to Braves (20-25), 11-9 | Wrigley Field (7-12) | 15-30 | |
| » Starters: Bob Hendley vs Bob Buhl | Ninth | 17 out |
| Wednesday, May 30 |
| » Lost to Astros (18-27), 8-6 | Wrigley Field (7-13) | 15-31 | Lost 2 |
| » Starters: Dean Stone vs Cal Koonce | Ninth | 18½ out |
| Thursday, May 31 |
| » Lost to Astros (19-27), 10-6 | Wrigley Field (7-14) | 15-32 | Lost 3 |
| » Starters: Bob Bruce vs Dick Ellsworth | Ninth | 18½ out |
| Friday, June 1 |
| » Lost to Reds (28-17), 5-2 | Wrigley Field (7-15) | 15-33 | Lost 4 |
| » Starters: Joey Jay vs Don Cardwell | Eighth | 19½ out |
| Saturday, June 2 |
| » Lost to Reds (29-17), 3-2 | Wrigley Field (7-16) | 15-34 | Lost 5 |
| » Starters: Johnny Klippstein vs Glen Hobbie | Ninth | 21 out |
| Sunday, June 3 |
| » Defeated Reds (29-18), 6-3 | Wrigley Field (8-16) | 16-34 | |
| » Starters: Moe Drabowsky vs Cal Koonce | Ninth | 21 out |
| Tuesday, June 5 |
| » Lost to Giants (40-15), 11-4 | Wrigley Field (8-17) | 16-35 | |
| » Manager: Charlie Metro |
| » Starters: Billy O'Dell vs Bob Buhl | Ninth | 22 out |
| Wednesday, June 6 |
| » Defeated Giants (40-16), 4-3 | Wrigley Field (9-17) | 17-35 | |
| » Starters: Mike McCormick vs Dick Ellsworth | Ninth | 21 out |
| Thursday, June 7 |
| » Defeated Giants (40-17), 4-3 | Wrigley Field (10-17) | 18-35 | Won 2 |
| » Starters: Billy Pierce vs Don Cardwell | Ninth | 20 out |
| Friday, June 8 |
| » Lost to Mets (13-36), 4-3 | Wrigley Field (10-18) | 18-36 | |
| » Starters: Jay Hook vs Glen Hobbie | Ninth | 20 out |
| » Defeated Mets (13-37), 3-2 | Wrigley Field (11-18) | 19-36 | |
| » Starters: Bob Miller vs Cal Koonce | Ninth | 20 out |
| Saturday, June 9 |
| » Lost to Mets (14-37), 11-6 | Wrigley Field (11-19) | 19-37 | |
| » Starters: Bob Moorhead vs Bob Buhl | Ninth | 20 out |
| Sunday, June 10 |
| » Lost to Mets (15-37), 2-1 | Wrigley Field (11-20) | 19-38 | Lost 2 |
| » Starters: Roger Craig vs Dick Ellsworth | Ninth | 21 out |
| » Defeated Mets (15-38), 5-4 | Wrigley Field (12-20) | 20-38 | |
| » Starters: Ray Daviault vs Bob Anderson | Ninth | 21 out |
| Monday, June 11 |
| » Lost to Pirates (32-25), 6-1 | Wrigley Field (12-21) | 20-39 | |
| » Starters: Joe Gibbon vs Don Cardwell | Ninth | 21½ out |
| Tuesday, June 12 |
| » Lost to Pirates (33-25), 4-3 | Wrigley Field (12-22) | 20-40 | Lost 2 |
| » Starters: Harvey Haddix vs Glen Hobbie | Ninth | 21½ out |
| Wednesday, June 13 |
| » Lost to Pirates (34-25), 6-4 | Wrigley Field (12-23) | 20-41 | Lost 3 |
| » Starters: Al McBean vs Cal Koonce | Ninth | 22½ out |
| Thursday, June 14 |
| » Lost to Pirates (35-25), 6-3 | Wrigley Field (12-24) | 20-42 | Lost 4 |
| » Starters: Bob Friend vs Dick Ellsworth | Eighth | 22½ out |
| Friday, June 15 |
| » Defeated Mets (16-41), 5-1 | Polo Grounds V (1-2) | 21-42 | |
| » Starters: Bob Anderson vs Roger Craig | Ninth | 21½ out |
| Saturday, June 16 |
| » Defeated Mets (16-42), 6-3 | Polo Grounds V (2-2) | 22-42 | Won 2 |
| » Starters: Don Cardwell vs Willard Hunter | Ninth | 20½ out |
| Future Cub Calvin Schiraldi is born in Houston, TX. |
| Sunday, June 17 |
| » Defeated Mets (16-43), 8-7 | Polo Grounds V (3-2) | 23-42 | Won 3 |
| » Starters: Glen Hobbie vs Al Jackson | Ninth | 20 out |
| » Defeated Mets (16-44), 4-3 | Polo Grounds V (4-2) | 24-42 | Won 4 |
| » Starters: Bob Buhl vs Bob Miller | Ninth | 20 out |
| Former Cub Mandy Brooks dies in Kirkwood, MO at the age of 65. |
| Tuesday, June 19 |
| » Defeated Phillies (27-36), 9-5 | Shibe Park (4-1) | 25-42 | Won 5 |
| » Starters: Cal Koonce vs Dennis Bennett | Ninth | 20½ out |
| Thursday, June 21 |
| » Lost to Phillies (28-36), 3-0 | Shibe Park (4-2) | 25-43 | |
| » Starters: Dick Ellsworth vs Art Mahaffey | Ninth | 20½ out |
| Friday, June 22 |
| » Lost to Pirates (39-29), 7-5 | Forbes Field (1-2) | 25-44 | Lost 2 |
| » Starters: Bob Anderson vs Joe Gibbon | Ninth | 20½ out |
| Saturday, June 23 |
| » Lost to Pirates (40-29), 4-3 | Forbes Field (1-3) | 25-45 | Lost 3 |
| » Starters: Don Cardwell vs Bob Friend | Eighth | 21½ out |
| Sunday, June 24 |
| » Defeated Pirates (40-30), 4-3 | Forbes Field (2-3) | 26-45 | |
| » Starters: Bob Buhl vs Al McBean | Ninth | 20 out |
| » Defeated Pirates (40-31), 8-4 | Forbes Field (3-3) | 27-45 | Won 2 |
| » Starters: Cal Koonce vs Earl Francis | Ninth | 20 out |
| Monday, June 25 |
| » Lost to Cardinals (39-31), 6-4 | Wrigley Field (12-25) | 27-46 | |
| » Starters: Ray Washburn vs Glen Hobbie | Ninth | 20 out |
| Tuesday, June 26 |
| » Lost to Cardinals (40-31), 15-3 | Wrigley Field (12-26) | 27-47 | Lost 2 |
| » Starters: Ernie Broglio vs Dick Ellsworth | Ninth | 20½ out |
| Wednesday, June 27 |
| » Lost to Cardinals (41-31), 4-0 | Wrigley Field (12-27) | 27-48 | Lost 3 |
| » Starters: Larry Jackson vs Don Cardwell | Ninth | 22 out |
| » Lost to Cardinals (42-31), 8-0 | Wrigley Field (12-28) | 27-49 | Lost 4 |
| » Starters: Ray Sadecki vs Bob Anderson | Ninth | 22 out |
| Thursday, June 28 |
| » Defeated Cardinals (42-32), 7-2 | Wrigley Field (13-28) | 28-49 | |
| » Starters: Bob Gibson vs Cal Koonce | Ninth | 21½ out |
| Friday, June 29 |
| » Defeated Braves (36-39), 4-0 | County Stadium (2-1) | 29-49 | Won 2 |
| » Starters: Bob Buhl vs Tony Cloninger | Eighth | 21 out |
| Saturday, June 30 |
| » Lost to Braves (37-39), 5-3 | County Stadium (2-2) | 29-50 | |
| » Starters: Dick Ellsworth vs Warren Spahn | Ninth | 22 out |
| Sunday, July 1 |
| » Lost to Braves (38-39), 1-0 | County Stadium (2-3) | 29-51 | Lost 2 |
| » Starters: Don Cardwell vs Bob Hendley | Ninth | 23 out |
| Monday, July 2 |
| » Defeated Reds (40-35), 6-5 | Crosley Field (1-3) | 30-51 | |
| » Starters: Cal Koonce vs Bob Purkey | Ninth | 23½ out |
| » Lost to Reds (41-35), 4-3 | Crosley Field (1-4) | 30-52 | |
| » Starters: Al Lary vs Ted Wills | Ninth | 23½ out |
| Tuesday, July 3 |
| » Lost to Reds (42-35), 6-1 | Crosley Field (1-5) | 30-53 | Lost 2 |
| » Starters: Bob Buhl vs Jim O'Toole | Ninth | 24 out |
| Wednesday, July 4 |
| » Lost to Reds (43-35), 8-6 | Crosley Field (1-6) | 30-54 | Lost 3 |
| » Starters: Dick Ellsworth vs Jim Maloney | Ninth | 25½ out |
| Friday, July 6 |
| » Lost to Braves (41-41), 5-3 | Wrigley Field (13-29) | 30-55 | Lost 4 |
| » Starters: Bob Hendley vs Don Cardwell | Ninth | 26 out |
| Saturday, July 7 |
| » Defeated Braves (41-42), 2-1 | Wrigley Field (14-29) | 31-55 | |
| » Starters: Bob Shaw vs Cal Koonce | Ninth | 25½ out |
| Sunday, July 8 |
| » Defeated Braves (41-43), 7-5 | Wrigley Field (15-29) | 32-55 | Won 2 |
| » Starters: Lew Burdette vs Bob Buhl | Ninth | 25½ out |
| » Lost to Braves (42-43), 5-3 | Wrigley Field (15-30) | 32-56 | |
| » Starters: Warren Spahn vs Al Lary | Ninth | 25½ out |
| Thursday, July 12 |
| » Lost to Reds (47-36), 8-4 | Wrigley Field (15-31) | 32-57 | Lost 2 |
| » Starters: Joey Jay vs Don Cardwell | Ninth | 26½ out |
| Friday, July 13 |
| » Defeated Reds (47-37), 1-0 | Wrigley Field (16-31) | 33-57 | |
| » Starters: Bob Purkey vs Cal Koonce | Ninth | 26½ out |
| Saturday, July 14 |
| » Defeated Reds (47-38), 6-3 | Wrigley Field (17-31) | 34-57 | Won 2 |
| » Starters: Jim O'Toole vs Glen Hobbie | Ninth | 26½ out |
| Sunday, July 15 |
| » Lost to Astros (34-53), 5-4 | Colt Stadium (0-4) | 34-58 | |
| » Starters: Bob Buhl vs Hal Woodeshick | Ninth | 26½ out |
| » Defeated Astros (34-54), 4-1 | Colt Stadium (1-4) | 35-58 | |
| » Starters: Dick Ellsworth vs Ken Johnson | Ninth | 26½ out |
| Tuesday, July 17 |
| » Lost to Cardinals (51-41), 8-6 | Sportsman's Park III (2-2) | 35-59 | |
| » Starters: Don Cardwell vs Larry Jackson | Ninth | 26½ out |
| Wednesday, July 18 |
| » Lost to Cardinals (52-41), 2-1 | Sportsman's Park III (2-3) | 35-60 | Lost 2 |
| » Starters: Cal Koonce vs Bob Gibson | Ninth | 27½ out |
| Thursday, July 19 |
| » Lost to Cardinals (53-41), 5-4 | Sportsman's Park III (2-4) | 35-61 | Lost 3 |
| » Starters: Glen Hobbie vs Ernie Broglio | Ninth | 27½ out |
| Friday, July 20 |
| » Lost to Dodgers (64-34), 8-2 | Wrigley Field (17-32) | 35-62 | Lost 4 |
| » Starters: Stan Williams vs Bob Buhl | Ninth | 28½ out |
| Saturday, July 21 |
| » Lost to Dodgers (65-34), 3-1 | Wrigley Field (17-33) | 35-63 | Lost 5 |
| » Starters: Don Drysdale vs Dick Ellsworth | Ninth | 29½ out |
| Sunday, July 22 |
| » Lost to Dodgers (66-34), 13-6 | Wrigley Field (17-34) | 35-64 | Lost 6 |
| » Starters: Joe Moeller vs Don Cardwell | Ninth | 30½ out |
| Monday, July 23 |
| » Lost to Phillies (46-55), 5-3 | Wrigley Field (17-35) | 35-65 | Lost 7 |
| » Starters: Cal McLish vs Cal Koonce | Ninth | 31½ out |
| Tuesday, July 24 |
| » Defeated Phillies (46-56), 5-3 | Wrigley Field (18-35) | 36-65 | |
| » Starters: Art Mahaffey vs Glen Hobbie | Ninth | 30½ out |
| Wednesday, July 25 |
| » Defeated Phillies (46-57), 5-2 | Wrigley Field (19-35) | 37-65 | Won 2 |
| » Starters: Dennis Bennett vs Bob Buhl | Ninth | 30½ out |
| Friday, July 27 |
| » Defeated Astros (36-64), 5-1 | Wrigley Field (20-35) | 38-65 | Won 3 |
| » Starters: Hal Woodeshick vs Dick Ellsworth | Eighth | 30½ out |
| Sunday, July 29 |
| » Defeated Astros (36-65), 4-2 | Wrigley Field (21-35) | 39-65 | Won 4 |
| » Starters: Bob Bruce vs Cal Koonce | Eighth | 31½ out |
| » Lost to Astros (37-65), 3-1 | Wrigley Field (21-36) | 39-66 | |
| » Starters: Ken Johnson vs Glen Hobbie | Eighth | 31½ out |
| Wednesday, August 1 |
| » Defeated Giants (67-40), 3-2 | Candlestick Park (1-4) | 40-66 | |
| » Starters: Bob Buhl vs Billy O'Dell | Eighth | 30½ out |
| Thursday, August 2 |
| » Lost to Giants (68-40), 4-3 | Candlestick Park (1-5) | 40-67 | |
| » Starters: Dick Ellsworth vs Billy Pierce | Eighth | 31½ out |
| Friday, August 3 |
| » Lost to Dodgers (73-36), 8-3 | Dodger Stadium (1-3) | 40-68 | Lost 2 |
| » Starters: Cal Koonce vs Don Drysdale | Ninth | 32½ out |
| Saturday, August 4 |
| » Lost to Dodgers (74-36), 5-3 | Dodger Stadium (1-4) | 40-69 | Lost 3 |
| » Starters: Glen Hobbie vs Stan Williams | Ninth | 33½ out |
| Sunday, August 5 |
| » Lost to Dodgers (75-36), 4-3 | Dodger Stadium (1-5) | 40-70 | Lost 4 |
| » Starters: Bob Buhl vs Phil Ortega | Ninth | 33½ out |
| » Defeated Dodgers (75-37), 4-2 | Dodger Stadium (2-5) | 41-70 | |
| » Starters: Don Cardwell vs Pete Richert | Ninth | 33½ out |
| Monday, August 6 |
| » Lost to Braves (59-53), 4-1 | County Stadium (2-4) | 41-71 | |
| » Starters: Dick Ellsworth vs Bob Shaw | Ninth | 34½ out |
| Tuesday, August 7 |
| » Lost to Braves (60-53), 4-1 | County Stadium (2-5) | 41-72 | Lost 2 |
| » Starters: Cal Koonce vs Lew Burdette | Ninth | 35½ out |
| Wednesday, August 8 |
| » Defeated Braves (60-54), 12-4 | County Stadium (3-5) | 42-72 | |
| » Starters: Glen Hobbie vs Bob Hendley | Eighth | 35½ out |
| Thursday, August 9 |
| » Lost to Braves (61-54), 1-0 | County Stadium (3-6) | 42-73 | |
| » Starters: Bob Buhl vs Tony Cloninger | Eighth | 36½ out |
| Friday, August 10 |
| » Defeated Pirates (63-50), 7-6 | Wrigley Field (22-36) | 43-73 | |
| » Starters: Bob Friend vs Don Cardwell | Eighth | 35½ out |
| Saturday, August 11 |
| » Lost to Pirates (64-50), 10-6 | Wrigley Field (22-37) | 43-74 | |
| » Starters: Vern Law vs Dick Ellsworth | Eighth | 35½ out |
| Sunday, August 12 |
| » Lost to Pirates (65-50), 5-4 | Wrigley Field (22-38) | 43-75 | Lost 2 |
| » Starters: Harvey Haddix vs Cal Koonce | Eighth | 35½ out |
| Future Cub Dave Pavlas is born in Frankfurt, W.Germany. |
| Tuesday, August 14 |
| » Lost to Giants (77-42), 9-2 | Wrigley Field (22-39) | 43-76 | Lost 3 |
| » Starters: Jack Sanford vs Glen Hobbie | Ninth | 35½ out |
| Wednesday, August 15 |
| » Defeated Giants (77-43), 7-5 | Wrigley Field (23-39) | 44-76 | |
| » Starters: Billy O'Dell vs Bob Buhl | Ninth | 34½ out |
| Thursday, August 16 |
| » Defeated Giants (77-44), 6-0 | Wrigley Field (24-39) | 45-76 | Won 2 |
| » Starters: Billy Pierce vs Don Cardwell | Eighth | 34½ out |
| Friday, August 17 |
| » Lost to Astros (44-75), 3-2 | Colt Stadium (1-5) | 45-77 | |
| » Starters: Dick Ellsworth vs Bob Bruce | Ninth | 35½ out |
| Saturday, August 18 |
| » Lost to Astros (45-75), 2-1 | Colt Stadium (1-6) | 45-78 | Lost 2 |
| » Starters: Cal Koonce vs George Brunet | Ninth | 35 out |
| » Defeated Astros (45-76), 6-5 | Colt Stadium (2-6) | 46-78 | |
| » Starters: Glen Hobbie vs Ken Johnson | Ninth | 35 out |
| Sunday, August 19 |
| » Defeated Astros (45-77), 4-3 | Colt Stadium (3-6) | 47-78 | Won 2 |
| » Starters: Bob Buhl vs Hal Woodeshick | Eighth | 35 out |
| Tuesday, August 21 |
| » Lost to Reds (77-49), 2-0 | Wrigley Field (24-40) | 47-79 | |
| » Starters: Jim Maloney vs Don Cardwell | Eighth | 35 out |
| Wednesday, August 22 |
| » Lost to Reds (78-49), 9-5 | Wrigley Field (24-41) | 47-80 | Lost 2 |
| » Starters: Jim O'Toole vs Dick Ellsworth | Eighth | 35 out |
| Future Cub Darrin Jackson is born in Los Angeles, CA. |
| Thursday, August 23 |
| » Lost to Reds (79-49), 14-3 | Wrigley Field (24-42) | 47-81 | Lost 3 |
| » Starters: Joe Nuxhall vs Cal Koonce | Eighth | 36 out |
| Friday, August 24 |
| » Defeated Braves (70-60), 7-2 | Wrigley Field (25-42) | 48-81 | |
| » Starters: Tony Cloninger vs Bob Buhl | Eighth | 35 out |
| Saturday, August 25 |
| » Lost to Braves (71-60), 10-1 | Wrigley Field (25-43) | 48-82 | |
| » Starters: Warren Spahn vs Don Cardwell | Eighth | 36 out |
| Sunday, August 26 |
| » Defeated Braves (71-61), 4-1 | Wrigley Field (26-43) | 49-82 | |
| » Starters: Denny Lemaster vs Dick Ellsworth | Eighth | 36 out |
| Tuesday, August 28 |
| » Lost to Pirates (77-55), 7-6 | Forbes Field (3-4) | 49-83 | |
| » Starters: Bob Buhl vs Vern Law | Eighth | 37 out |
| Wednesday, August 29 |
| » Lost to Pirates (78-55), 5-2 | Forbes Field (3-5) | 49-84 | Lost 2 |
| » Starters: Cal Koonce vs Bob Friend | Eighth | 38 out |
| Thursday, August 30 |
| » Lost to Pirates (79-55), 5-3 | Forbes Field (3-6) | 49-85 | Lost 3 |
| » Starters: Don Cardwell vs Al McBean | Ninth | 38 out |
| Saturday, September 1 |
| » Defeated Astros (49-85), 4-3 | Wrigley Field (27-43) | 50-85 | |
| » Starters: George Brunet vs Dick Ellsworth | Eighth | 38½ out |
| Sunday, September 2 |
| » Lost to Astros (50-85), 3-1 | Wrigley Field (27-44) | 50-86 | |
| » Starters: Ken Johnson vs Bob Buhl | Ninth | 39½ out |
| Monday, September 3 |
| » Defeated Cardinals (73-64), 6-2 | Sportsman's Park III (3-4) | 51-86 | |
| » Starters: Glen Hobbie vs Bob Gibson | Eighth | 38 out |
| » Defeated Cardinals (73-65), 5-2 | Sportsman's Park III (4-4) | 52-86 | Won 2 |
| » Starters: Don Cardwell vs Curt Simmons | Eighth | 38 out |
| Future Cub Dave Clark is born in Tupelo, MS. |
| Tuesday, September 4 |
| » Lost to Cardinals (74-65), 7-1 | Sportsman's Park III (4-5) | 52-87 | |
| » Starters: Cal Koonce vs Larry Jackson | Eighth | 39 out |
| Wednesday, September 5 |
| » Lost to Reds (86-55), 7-5 | Crosley Field (1-7) | 52-88 | Lost 2 |
| » Starters: Dick Ellsworth vs Jim Maloney | Ninth | 39½ out |
| » Lost to Reds (87-55), 10-3 | Crosley Field (1-8) | 52-89 | Lost 3 |
| » Starters: Paul Toth vs Joe Nuxhall | Ninth | 39½ out |
| Friday, September 7 |
| » Lost to Giants (90-51), 6-5 | Candlestick Park (1-6) | 52-90 | Lost 4 |
| » Starters: Bob Buhl vs Jack Sanford | Ninth | 39 out |
| Saturday, September 8 |
| » Lost to Giants (91-51), 7-2 | Candlestick Park (1-7) | 52-91 | Lost 5 |
| » Starters: Don Cardwell vs Billy Pierce | Ninth | 40 out |
| Sunday, September 9 |
| » Lost to Giants (92-51), 5-4 | Candlestick Park (1-8) | 52-92 | Lost 6 |
| » Starters: Glen Hobbie vs Mike McCormick | Ninth | 41 out |
| Monday, September 10 |
| » Lost to Dodgers (94-51), 8-1 | Dodger Stadium (2-6) | 52-93 | Lost 7 |
| » Starters: Dick Ellsworth vs Don Drysdale | Ninth | 42 out |
| » Major-league debuts: Jack Smith (Dodgers) |
| Tuesday, September 11 |
| » Lost to Dodgers (95-51), 3-1 | Dodger Stadium (2-7) | 52-94 | Lost 8 |
| » Starters: Bob Buhl vs Stan Williams | Ninth | 43 out |
| Thursday, September 13 |
| » Major-league debuts: Pete Smith (Red Sox) |
| Friday, September 14 |
| » Lost to Dodgers (97-51), 13-7 | Wrigley Field (27-45) | 52-95 | Lost 9 |
| » Starters: Johnny Podres vs Don Cardwell | Ninth | 44½ out |
| Saturday, September 15 |
| » Lost to Dodgers (98-51), 6-4 | Wrigley Field (27-46) | 52-96 | Lost 10 |
| » Starters: Don Drysdale vs Cal Koonce | Ninth | 45½ out |
| Sunday, September 16 |
| » Defeated Dodgers (98-52), 5-0 | Wrigley Field (28-46) | 53-96 | |
| » Starters: Stan Williams vs Bob Buhl | Ninth | 44½ out |
| Monday, September 17 |
| » Defeated Cardinals (77-73), 8-4 | Wrigley Field (29-46) | 54-96 | Won 2 |
| » Starters: Ray Washburn vs Dick Ellsworth | Ninth | 43½ out |
| Tuesday, September 18 |
| » Defeated Cardinals (77-74), 4-3 | Wrigley Field (30-46) | 55-96 | Won 3 |
| » Starters: Harvey Branch vs Paul Toth | Ninth | 42½ out |
| Wednesday, September 19 |
| » Lost to Phillies (76-76), 4-3 | Shibe Park (4-3) | 55-97 | |
| » Starters: Morrie Steevens vs Chris Short | Ninth | 43½ out |
| Future Cub Randy Myers is born in Vancouver, WA. |
| Thursday, September 20 |
| » Lost to Phillies (77-76), 3-1 | Shibe Park (4-4) | 55-98 | Lost 2 |
| » Starters: Bob Buhl vs Dennis Bennett | Ninth | 43½ out |
| » Defeated Phillies (77-77), 4-1 | Shibe Park (5-4) | 56-98 | |
| » Starters: Cal Koonce vs Jack Hamilton | Ninth | 43½ out |
| Friday, September 21 |
