| Sunday, January 11 |
| Future Pirate Lloyd McClendon is born in Gary, IN. |
| Wednesday, January 14 |
| Former Pirate John Ganzel dies in Orlando, FL at the age of 85. |
| Monday, February 23 |
| Future Pirate Eddie Vargas is born in Guanica, P.R. |
| Thursday, April 9 |
| » Lost to Reds (1-0), 4-1 | Crosley Field (0-1) | 0-1 | |
| » Starters: Ron Kline vs Bob Purkey | Third | 1 out |
| Friday, April 10 |
| » Lost to Braves (1-0), 8-0 | Forbes Field (0-1) | 0-2 | Lost 2 |
| » Starters: Warren Spahn vs Bob Friend | Fifth | 1½ out |
| Saturday, April 11 |
| » Lost to Braves (2-0), 4-3 | Forbes Field (0-2) | 0-3 | Lost 3 |
| » Starters: Lew Burdette vs Vern Law | Sixth | 2½ out |
| Tuesday, April 14 |
| » Lost to Reds (2-1), 3-2 | Crosley Field (0-2) | 0-4 | Lost 4 |
| » Starters: George Witt vs Bob Purkey | Seventh | 3½ out |
| Wednesday, April 15 |
| » Lost to Reds (3-1), 10-5 | Crosley Field (0-3) | 0-5 | Lost 5 |
| » Starters: Bob Friend vs Joe Nuxhall | Seventh | 4 out |
| » Major-league debuts: Freddie Green (Pirates) |
| Friday, April 17 |
| » Tied Braves, 2-2 | County Stadium (0-0) | 0-5 | |
| » Starters: Harvey Haddix vs Bob Rush | Eighth | 4½ out |
| » Major-league debuts: Chuck Cottier (Braves) |
| Saturday, April 18 |
| » Defeated Braves (4-1), 11-5 | County Stadium (1-0) | 1-5 | |
| » Starters: Vern Law vs Bob Buhl | Seventh | 3½ out |
| » Major-league debuts: Bob Giggie (Braves) |
| Sunday, April 19 |
| » Major-league debuts: Chris Short (Phillies) |
| Future Pirate R.J. Reynolds is born in Sacramento, CA. |
| Wednesday, April 22 |
| » Defeated Reds (4-5), 9-8 | Forbes Field (1-2) | 2-5 | Won 2 |
| » Starters: Joe Nuxhall vs Bob Friend | Seventh | 4 out |
| Thursday, April 23 |
| » Lost to Reds (5-5), 5-2 | Forbes Field (1-3) | 2-6 | |
| » Starters: Brooks Lawrence vs George Witt | Seventh | 4 out |
| Friday, April 24 |
| » Defeated Phillies (4-5), 8-5 | Shibe Park (1-0) | 3-6 | |
| » Starters: Ron Kline vs Jim Owens | Seventh | 4 out |
| Saturday, April 25 |
| » Defeated Phillies (4-6), 4-2 | Shibe Park (2-0) | 4-6 | Won 2 |
| » Starters: Harvey Haddix vs Seth Morehead | Sixth | 3 out |
| Sunday, April 26 |
| » Defeated Phillies (4-7), 9-2 | Shibe Park (3-0) | 5-6 | Won 3 |
| » Starters: Vern Law vs Don Cardwell | Sixth | 3 out |
| » Lost to Phillies (5-7), 10-5 | Shibe Park (3-1) | 5-7 | |
| » Starters: Bob Friend vs Chris Short | Sixth | 3 out |
| Monday, April 27 |
| » Lost to Dodgers (10-5), 9-3 | Forbes Field (1-4) | 5-8 | Lost 2 |
| » Starters: Don Drysdale vs George Witt | Seventh | 4 out |
| Wednesday, April 29 |
| » Defeated Giants (9-7), 3-2 | Forbes Field (2-4) | 6-8 | |
| » Starters: Johnny Antonelli vs Ron Kline | Seventh | 3 out |
| Friday, May 1 |
| » Lost to Cardinals (5-13), 7-6 | Forbes Field (2-5) | 6-9 | |
| » Starters: Vinegar Bend Mizell vs Bob Friend | Seventh | 3½ out |
| Saturday, May 2 |
| » Defeated Cardinals (5-14), 2-1 | Forbes Field (3-5) | 7-9 | |
| » Starters: Lindy McDaniel vs Harvey Haddix | Sixth | 3 out |
| Sunday, May 3 |
| » Defeated Cardinals (5-15), 4-3 | Forbes Field (4-5) | 8-9 | Won 2 |
| » Starters: Larry Jackson vs Vern Law | Fifth | 3 out |
| » Lost to Cardinals (6-15), 3-1 | Forbes Field (4-6) | 8-10 | |
| » Starters: Gary Blaylock vs Bennie Daniels | Fifth | 3 out |
| Monday, May 4 |
| » Defeated Cubs (10-11), 2-1 | Forbes Field (5-6) | 9-10 | |
| » Starters: Bob Anderson vs Ron Kline | Sixth | 2½ out |
| Tuesday, May 5 |
| » Lost to Cubs (11-11), 6-3 | Forbes Field (5-7) | 9-11 | |
| » Starters: Glen Hobbie vs Bob Friend | Sixth | 3 out |
| Wednesday, May 6 |
| » Lost to Cubs (12-11), 3-0 | Forbes Field (5-8) | 9-12 | Lost 2 |
| » Starters: Dave Hillman vs Harvey Haddix | Sixth | 4 out |
| Thursday, May 7 |
| » Defeated Phillies (9-12), 5-4 | Forbes Field (6-8) | 10-12 | |
| » Starters: Jim Owens vs Vern Law | Sixth | 3½ out |
| Friday, May 8 |
| » Lost to Phillies (10-12), 8-1 | Forbes Field (6-9) | 10-13 | |
| » Starters: Gene Conley vs George Witt | Seventh | 3½ out |
| Saturday, May 9 |
| » Defeated Phillies (10-13), 9-1 | Forbes Field (7-9) | 11-13 | |
| » Starters: Ruben Gomez vs Ron Kline | Sixth | 3½ out |
| Sunday, May 10 |
| » Lost to Phillies (11-13), 6-3 | Forbes Field (7-10) | 11-14 | |
| » Starters: Robin Roberts vs Bob Friend | Sixth | 3½ out |
| » Defeated Phillies (11-14), 7-6 | Forbes Field (8-10) | 12-14 | |
| » Starters: Ray Semproch vs Harvey Haddix | Sixth | 3½ out |
| Monday, May 11 |
| » Lost to Giants (14-12), 14-4 | Seals Stadium (0-1) | 12-15 | |
| » Starters: Bennie Daniels vs Jack Sanford | Sixth | 4½ out |
| Tuesday, May 12 |
| » Defeated Giants (14-13), 6-5 | Seals Stadium (1-1) | 13-15 | |
| » Starters: Vern Law vs Johnny Antonelli | Sixth | 4 out |
| Wednesday, May 13 |
| » Defeated Dodgers (18-13), 6-4 | Los Angeles Memorial Coliseum (1-0) | 14-15 | Won 2 |
| » Starters: Ron Kline vs Don Drysdale | Sixth | 3½ out |
| Thursday, May 14 |
| » Defeated Dodgers (18-14), 7-6 | Los Angeles Memorial Coliseum (2-0) | 15-15 | Won 3 |
| » Starters: Bob Friend vs Johnny Podres | Fifth | 3½ out |
| Saturday, May 16 |
| » Lost to Cubs (17-16), 3-2 | Wrigley Field (0-1) | 15-16 | |
| » Starters: Harvey Haddix vs Moe Drabowsky | Sixth | 4½ out |
| Future Pirate Bob Patterson is born in Jacksonville, FL. Future Pirate Mitch Webster is born in Larned, KS. |
| Sunday, May 17 |
| » Defeated Cubs (17-17), 5-4 | Wrigley Field (1-1) | 16-16 | |
| » Starters: Vern Law vs Bob Anderson | Sixth | 5 out |
| » Lost to Cubs (18-17), 7-6 | Wrigley Field (1-2) | 16-17 | |
| » Starters: Bennie Daniels vs Glen Hobbie | Sixth | 5 out |
| Tuesday, May 19 |
| » Lost to Cardinals (14-20), 8-2 | Sportsman's Park III (0-1) | 16-18 | Lost 2 |
| » Starters: Ron Kline vs Larry Jackson | Fifth | 6½ out |
| Wednesday, May 20 |
| » Lost to Cardinals (15-20), 11-1 | Sportsman's Park III (0-2) | 16-19 | Lost 3 |
| » Starters: Bob Friend vs Vinegar Bend Mizell | Sixth | 6½ out |
| Thursday, May 21 |
| » Defeated Cardinals (15-21), 7-2 | Sportsman's Park III (1-2) | 17-19 | |
| » Starters: Harvey Haddix vs Lindy McDaniel | Fifth | 6 out |
| Friday, May 22 |
| » Defeated Reds (18-18), 4-3 | Forbes Field (9-10) | 18-19 | Won 2 |
| » Starters: Bob Purkey vs Vern Law | Sixth | 6 out |
| Saturday, May 23 |
| » Defeated Reds (18-19), 6-5 | Forbes Field (10-10) | 19-19 | Won 3 |
| » Starters: Orlando Pena vs Bennie Daniels | Fourth | 5 out |
| Sunday, May 24 |
| » Defeated Reds (18-20), 2-1 | Forbes Field (11-10) | 20-19 | Won 4 |
| » Starters: Brooks Lawrence vs Ron Kline | Third | 4 out |
| » Defeated Reds (18-21), 5-4 | Forbes Field (12-10) | 21-19 | Won 5 |
| » Starters: Willard Schmidt vs Bob Friend | Third | 4 out |
| Monday, May 25 |
| Former Pirate Dave Brain dies in Los Angeles, CA at the age of 81. |
| Tuesday, May 26 |
| » Lost to Braves (24-14), 1-0 | County Stadium (1-1) | 21-20 | |
| » Starters: Harvey Haddix vs Lew Burdette | Fourth | 4½ out |
| » Major-league debuts: Joe Christopher (Pirates) |
| Future Pirate Dann Bilardello is born in Santa Cruz, CA. |
| Wednesday, May 27 |
| » Lost to Braves (25-14), 4-3 | County Stadium (1-2) | 21-21 | Lost 2 |
| » Starters: Vern Law vs Warren Spahn | Fourth | 5½ out |
| Thursday, May 28 |
| » Defeated Braves (25-15), 3-0 | County Stadium (2-2) | 22-21 | |
| » Starters: Bob Friend vs Joey Jay | Third | 4½ out |
| Friday, May 29 |
| » Lost to Reds (21-22), 8-5 | Crosley Field (0-4) | 22-22 | |
| » Starters: Ron Kline vs Brooks Lawrence | Fourth | 5½ out |
| Saturday, May 30 |
| » Defeated Reds (21-23), 3-1 | Crosley Field (1-4) | 23-22 | |
| » Starters: Bennie Daniels vs Jim O'Toole | Fourth | 5½ out |
| Sunday, May 31 |
| » Defeated Reds (21-24), 6-2 | Crosley Field (2-4) | 24-22 | Won 2 |
| » Starters: Vern Law vs Bob Purkey | Third | 4½ out |
| » Defeated Reds (21-25), 14-11 | Crosley Field (3-4) | 25-22 | Won 3 |
| » Starters: Al Jackson vs Don Newcombe | Third | 4½ out |
| Tuesday, June 2 |
| » Defeated Cardinals (19-27), 3-0 | Forbes Field (13-10) | 26-22 | Won 4 |
| » Starters: Larry Jackson vs Harvey Haddix | Third | 4 out |
| Wednesday, June 3 |
| » Defeated Cardinals (19-28), 5-3 | Forbes Field (14-10) | 27-22 | Won 5 |
| » Starters: Vinegar Bend Mizell vs Bob Friend | Third | 4 out |
| Thursday, June 4 |
| » Defeated Cardinals (19-29), 9-3 | Forbes Field (15-10) | 28-22 | Won 6 |
| » Starters: Ernie Broglio vs Ron Kline | Third | 3 out |
| Friday, June 5 |
| » Lost to Cubs (25-25), 10-5 | Forbes Field (15-11) | 28-23 | |
| » Starters: Glen Hobbie vs Vern Law | Third | 3 out |
| Saturday, June 6 |
| » Lost to Cubs (26-25), 8-2 | Forbes Field (15-12) | 28-24 | Lost 2 |
| » Starters: Moe Drabowsky vs Bennie Daniels | Third | 3 out |
| Future Pirate Doug Frobel is born in Ottawa, ON. |
| Sunday, June 7 |
| » Lost to Cubs (27-25), 4-2 | Forbes Field (15-13) | 28-25 | Lost 3 |
| » Starters: John Buzhardt vs Harvey Haddix | Fourth | 4½ out |
| » Lost to Cubs (28-25), 1-0 | Forbes Field (15-14) | 28-26 | Lost 4 |
| » Starters: Elmer Singleton vs Bob Friend | Fourth | 4½ out |
| Monday, June 8 |
| » Defeated Giants (30-24), 12-9 | Forbes Field (16-14) | 29-26 | |
| » Starters: Stu Miller vs Ron Kline | Third | 4½ out |
| Tuesday, June 9 |
| » Lost to Giants (31-24), 6-2 | Forbes Field (16-15) | 29-27 | |
| » Starters: Johnny Antonelli vs Vern Law | Fourth | 4½ out |
| Wednesday, June 10 |
| » Lost to Giants (32-24), 11-7 | Forbes Field (16-16) | 29-28 | Lost 2 |
| » Starters: Sam Jones vs George Witt | Fourth | 4½ out |
| Thursday, June 11 |
| » Defeated Giants (32-25), 12-9 | Forbes Field (17-16) | 30-28 | |
| » Starters: Jack Sanford vs Bob Friend | Fourth | 4½ out |
| Friday, June 12 |
| » Lost to Dodgers (31-27), 9-6 | Forbes Field (17-17) | 30-29 | |
| » Starters: Don Drysdale vs Harvey Haddix | Fifth | 4½ out |
| Saturday, June 13 |
| » Defeated Dodgers (31-28), 5-3 | Forbes Field (18-17) | 31-29 | |
| » Starters: Sandy Koufax vs Ron Kline | Fourth | 4½ out |
| Sunday, June 14 |
| » Defeated Dodgers (31-29), 6-3 | Forbes Field (19-17) | 32-29 | Won 2 |
| » Starters: Stan Williams vs George Witt | Third | 3 out |
| » Defeated Dodgers (31-30), 5-2 | Forbes Field (20-17) | 33-29 | Won 3 |
| » Starters: Carl Erskine vs Vern Law | Third | 3 out |
| Tuesday, June 16 |
| » Defeated Cubs (31-30), 5-2 | Wrigley Field (2-2) | 34-29 | Won 4 |
| » Starters: Bob Friend vs Dave Hillman | Third | 2½ out |
| Wednesday, June 17 |
| » Lost to Cubs (32-30), 5-2 | Wrigley Field (2-3) | 34-30 | |
| » Starters: Harvey Haddix vs John Buzhardt | Third | 2 out |
| Thursday, June 18 |
| » Defeated Cubs (32-31), 4-2 | Wrigley Field (3-3) | 35-30 | |
| » Starters: Ron Kline vs Moe Drabowsky | Third | 2 out |
| Friday, June 19 |
| » Defeated Cardinals (28-34), 6-0 | Sportsman's Park III (2-2) | 36-30 | Won 2 |
| » Starters: Vern Law vs Dick Ricketts | Third | 1½ out |
| Saturday, June 20 |
| » Lost to Cardinals (29-34), 5-2 | Sportsman's Park III (2-3) | 36-31 | |
| » Starters: Bob Friend vs Vinegar Bend Mizell | Third | 2 out |
| Sunday, June 21 |
| » Lost to Cardinals (30-34), 5-1 | Sportsman's Park III (2-4) | 36-32 | Lost 2 |
| » Starters: Harvey Haddix vs Larry Jackson | Third | 2½ out |
| » Defeated Cardinals (30-35), 10-8 | Sportsman's Park III (3-4) | 37-32 | |
| » Starters: Al Jackson vs Ernie Broglio | Third | 2½ out |
| Monday, June 22 |
| » Lost to Giants (38-30), 4-1 | Seals Stadium (1-2) | 37-33 | |
| » Starters: Ron Kline vs Eddie Fisher | Third | 3 out |
| » Major-league debuts: Eddie Fisher (Giants) |
| Tuesday, June 23 |
| » Defeated Giants (38-31), 5-1 | Seals Stadium (2-2) | 38-33 | |
| » Starters: Vern Law vs Sam Jones | Third | 3 out |
| Wednesday, June 24 |
| » Lost to Giants (39-31), 4-3 | Seals Stadium (2-3) | 38-34 | |
| » Starters: Bob Friend vs Johnny Antonelli | Fourth | 4 out |
| Thursday, June 25 |
| » Defeated Giants (39-32), 3-1 | Seals Stadium (3-3) | 39-34 | |
| » Starters: Harvey Haddix vs Stu Miller | Fourth | 3 out |
| Future Pirate Alejandro Pena is born in Cambiaso, D.R. |
| Friday, June 26 |
| » Lost to Dodgers (41-33), 6-5 | Los Angeles Memorial Coliseum (2-1) | 39-35 | |
| » Starters: Ron Kline vs Johnny Podres | Fourth | 4 out |
| Saturday, June 27 |
| » Lost to Dodgers (42-33), 3-0 | Los Angeles Memorial Coliseum (2-2) | 39-36 | Lost 2 |
| » Starters: Vern Law vs Sandy Koufax | Fourth | 4 out |
| Sunday, June 28 |
| » Lost to Dodgers (43-33), 9-4 | Los Angeles Memorial Coliseum (2-3) | 39-37 | Lost 3 |
| » Starters: Bob Friend vs Danny McDevitt | Fourth | 5 out |
| Former Pirate Joe Sugden dies in Philadelphia, PA at the age of 89. |
| Tuesday, June 30 |
| » Defeated Phillies (26-46), 4-3 | Shibe Park (4-1) | 40-37 | |
| » Starters: Harvey Haddix vs Robin Roberts | Fourth | 4 out |
| Wednesday, July 1 |
| » Lost to Phillies (27-46), 1-0 | Shibe Park (4-2) | 40-38 | |
| » Starters: Ron Kline vs Gene Conley | Fourth | 4½ out |
| Thursday, July 2 |
| » Defeated Braves (42-32), 4-3 | Forbes Field (21-17) | 41-38 | |
| » Starters: Warren Spahn vs Vern Law | Fourth | 3½ out |
| Friday, July 3 |
| » Lost to Braves (43-32), 6-0 | Forbes Field (21-18) | 41-39 | |
| » Starters: Juan Pizarro vs George Witt | Fourth | 4½ out |
| Saturday, July 4 |
| » Defeated Reds (35-43), 4-3 | Forbes Field (22-18) | 42-39 | |
| » Starters: Joe Nuxhall vs Bob Friend | Fourth | 4 out |
| Sunday, July 5 |
| » Defeated Reds (35-44), 7-5 | Forbes Field (23-18) | 43-39 | Won 2 |
| » Starters: Bob Purkey vs Harvey Haddix | Fourth | 3 out |
| » Defeated Reds (35-45), 3-2 | Forbes Field (24-18) | 44-39 | Won 3 |
| » Starters: Jim Brosnan vs Ron Kline | Fourth | 3 out |
| Thursday, July 9 |
| » Defeated Cubs (39-42), 4-3 | Forbes Field (25-18) | 45-39 | Won 4 |
| » Starters: Bob Anderson vs Vern Law | Fourth | 3 out |
| Friday, July 10 |
| » Defeated Cubs (39-43), 7-6 | Forbes Field (26-18) | 46-39 | Won 5 |
| » Starters: Glen Hobbie vs Bob Friend | Fourth | 3 out |
| Saturday, July 11 |
| » Lost to Cubs (40-43), 5-1 | Forbes Field (26-19) | 46-40 | |
| » Starters: Dave Hillman vs Ron Kline | Fourth | 4 out |
| Sunday, July 12 |
| » Defeated Cardinals (40-44), 6-5 | Forbes Field (27-19) | 47-40 | |
| » Starters: Ernie Broglio vs Harvey Haddix | Fourth | 3½ out |
| » Lost to Cardinals (41-44), 8-6 | Forbes Field (27-20) | 47-41 | |
| » Starters: Dick Ricketts vs George Witt | Fourth | 3½ out |
| Tuesday, July 14 |
| » Defeated Dodgers (49-40), 9-1 | Forbes Field (28-20) | 48-41 | |
| » Starters: Johnny Podres vs Vern Law | Fourth | 2½ out |
| Wednesday, July 15 |
| » Lost to Dodgers (50-40), 3-0 | Forbes Field (28-21) | 48-42 | |
| » Starters: Don Drysdale vs Bob Friend | Fourth | 3 out |
| Thursday, July 16 |
| Former Pirate Bob Coleman dies in Boston, MA at the age of 69. |
| Friday, July 17 |
| » Lost to Giants (51-38), 4-1 | Forbes Field (28-22) | 48-43 | Lost 2 |
| » Starters: Sam Jones vs Ron Kline | Fourth | 4 out |
| Saturday, July 18 |
| » Lost to Giants (52-38), 4-3 | Forbes Field (28-23) | 48-44 | Lost 3 |
| » Starters: Eddie Fisher vs Harvey Haddix | Fourth | 5 out |
| Sunday, July 19 |
| » Defeated Giants (52-39), 3-2 | Forbes Field (29-23) | 49-44 | |
| » Starters: Stu Miller vs Vern Law | Fourth | 4 out |
| Tuesday, July 21 |
| » Lost to Phillies (36-55), 4-2 | Forbes Field (29-24) | 49-45 | |
| » Starters: Robin Roberts vs Bob Friend | Fourth | 3½ out |
| Former Pirate Bill Hoffer dies in Cedar Rapids, IA at the age of 89. |
| Wednesday, July 22 |
| » Lost to Phillies (37-55), 11-4 | Forbes Field (29-25) | 49-46 | Lost 2 |
| » Starters: Gene Conley vs Ron Kline | Fourth | 4½ out |
| Friday, July 24 |
| » Lost to Braves (48-43), 8-0 | County Stadium (2-3) | 49-47 | Lost 3 |
| » Starters: Harvey Haddix vs Juan Pizarro | Fourth | 6 out |
| Saturday, July 25 |
| » Lost to Braves (49-43), 3-0 | County Stadium (2-4) | 49-48 | Lost 4 |
| » Starters: Vern Law vs Lew Burdette | Fourth | 6 out |
| Sunday, July 26 |
| » Lost to Braves (50-43), 4-0 | County Stadium (2-5) | 49-49 | Lost 5 |
| » Starters: Bob Friend vs Warren Spahn | Fifth | 6½ out |
| » Lost to Braves (51-43), 2-1 | County Stadium (2-6) | 49-50 | Lost 6 |
| » Starters: George Witt vs Bob Buhl | Fifth | 6½ out |
| Monday, July 27 |
| » Lost to Braves (52-43), 5-2 | County Stadium (2-7) | 49-51 | Lost 7 |
| » Starters: Ron Kline vs Joey Jay | Fifth | 7 out |
| Tuesday, July 28 |
| » Lost to Dodgers (56-46), 9-4 | Los Angeles Memorial Coliseum (2-4) | 49-52 | Lost 8 |
| » Starters: Bennie Daniels vs Larry Sherry | Fifth | 7 out |
| Wednesday, July 29 |
| » Lost to Dodgers (57-46), 2-0 | Los Angeles Memorial Coliseum (2-5) | 49-53 | Lost 9 |
| » Starters: Vern Law vs Roger Craig | Fifth | 7½ out |
| Future Pirate Dave LaPoint is born in Glens Falls, NY. |
| Thursday, July 30 |
| » Defeated Dodgers (57-47), 5-4 | Los Angeles Memorial Coliseum (3-5) | 50-53 | |
| » Starters: Bob Friend vs Johnny Podres | Fifth | 7 out |
| Friday, July 31 |
| » Lost to Giants (57-45), 4-3 | Seals Stadium (3-4) | 50-54 | |
| » Starters: Harvey Haddix vs Jack Sanford | Fifth | 8 out |
| Future Pirate Mike Bielecki is born in Baltimore, MD. |
| Saturday, August 1 |
| » Lost to Giants (58-45), 9-5 | Seals Stadium (3-5) | 50-55 | Lost 2 |
| » Starters: George Witt vs Sam Jones | Fifth | 9 out |
| Sunday, August 2 |
| » Lost to Giants (59-45), 5-3 | Seals Stadium (3-6) | 50-56 | Lost 3 |
| » Starters: Ron Kline vs Johnny Antonelli | Fifth | 10 out |
| Monday, August 3 |
| Future Pirate Jim Gott is born in Hollywood, CA. |
| Tuesday, August 4 |
| » Defeated Cardinals (50-57), 7-3 | Sportsman's Park III (4-4) | 51-56 | |
| » Starters: Vern Law vs Bob Gibson | Fifth | 9 out |
| Wednesday, August 5 |
| » Lost to Cardinals (51-57), 3-0 | Sportsman's Park III (4-5) | 51-57 | |
| » Starters: Bob Friend vs Ernie Broglio | Sixth | 10 out |
| Thursday, August 6 |
| » Defeated Cardinals (51-58), 18-2 | Sportsman's Park III (5-5) | 52-57 | |
| » Starters: Harvey Haddix vs Larry Jackson | Fifth | 10 out |
| Friday, August 7 |
| » Lost to Cubs (52-55), 4-0 | Wrigley Field (3-4) | 52-58 | |
| » Starters: Ron Kline vs Moe Drabowsky | Fifth | 11 out |
| Saturday, August 8 |
| » Defeated Cubs (52-56), 4-3 | Wrigley Field (4-4) | 53-58 | |
| » Starters: George Witt vs Bob Anderson | Sixth | 10 out |
| Sunday, August 9 |
| » Defeated Cubs (52-57), 5-3 | Wrigley Field (5-4) | 54-58 | Won 2 |
| » Starters: Vern Law vs Dave Hillman | Fourth | 10 out |
| Tuesday, August 11 |
| » Lost to Phillies (47-64), 6-4 | Shibe Park (4-3) | 54-59 | |
| » Starters: Bob Friend vs Don Cardwell | Fifth | 11½ out |
| Wednesday, August 12 |
| » Defeated Phillies (47-65), 6-2 | Shibe Park (5-3) | 55-59 | |
| » Starters: Harvey Haddix vs Robin Roberts | Fifth | 11 out |
| Friday, August 14 |
| » Defeated Braves (61-51), 2-1 | Forbes Field (30-25) | 56-59 | Won 2 |
| » Starters: Joey Jay vs Vern Law | Fifth | 9½ out |
| Saturday, August 15 |
| » Defeated Braves (61-52), 10-8 | Forbes Field (31-25) | 57-59 | Won 3 |
| » Starters: Lew Burdette vs Ron Kline | Fifth | 9½ out |
| Sunday, August 16 |
| » Defeated Braves (61-53), 2-1 | Forbes Field (32-25) | 58-59 | Won 4 |
| » Starters: Juan Pizarro vs Bob Friend | Fifth | 9 out |
| » Lost to Braves (62-53), 5-2 | Forbes Field (32-26) | 58-60 | |
| » Starters: Warren Spahn vs Bennie Daniels | Fifth | 9 out |
| Monday, August 17 |
| » Defeated Cubs (57-59), 7-6 | Forbes Field (33-26) | 59-60 | |
| » Starters: Dave Hillman vs Harvey Haddix | Fourth | 9 out |
| Wednesday, August 19 |
| » Defeated Cardinals (57-66), 4-2 | Forbes Field (34-26) | 60-60 | Won 2 |
| » Starters: Bob Gibson vs Vern Law | Fourth | 7½ out |
| Thursday, August 20 |
| » Defeated Cardinals (57-67), 3-1 | Forbes Field (35-26) | 61-60 | Won 3 |
| » Starters: Ernie Broglio vs Bob Friend | Fourth | 7½ out |
| Friday, August 21 |
| » Lost to Dodgers (68-55), 6-5 | Forbes Field (35-27) | 61-61 | |
| » Starters: Johnny Podres vs Ron Kline | Fourth | 9 out |
| Saturday, August 22 |
| » Defeated Dodgers (68-56), 2-0 | Forbes Field (36-27) | 62-61 | |
| » Starters: Roger Craig vs Bennie Daniels | Fourth | 9 out |
| Sunday, August 23 |
| » Defeated Dodgers (68-57), 9-2 | Forbes Field (37-27) | 63-61 | Won 2 |
| » Starters: Don Drysdale vs Harvey Haddix | Fourth | 8 out |
| » Defeated Dodgers (68-58), 4-3 | Forbes Field (38-27) | 64-61 | Won 3 |
| » Starters: Larry Sherry vs Vern Law | Fourth | 8 out |
| Monday, August 24 |
| » Defeated Giants (71-53), 6-0 | Forbes Field (39-27) | 65-61 | Won 4 |
| » Starters: Sam Jones vs Bob Friend | Fourth | 7 out |
| Tuesday, August 25 |
| » Lost to Giants (72-53), 12-5 | Forbes Field (39-28) | 65-62 | |
| » Starters: Johnny Antonelli vs Ron Kline | Fourth | 8 out |
| Wednesday, August 26 |
| » Defeated Giants (72-54), 5-4 | Forbes Field (40-28) | 66-62 | |
| » Starters: Jack Sanford vs Bennie Daniels | Fourth | 7 out |
| Friday, August 28 |
| » Defeated Phillies (54-76), 9-0 | Forbes Field (41-28) | 67-62 | Won 2 |
| » Starters: Ed Keegan vs Vern Law | Fourth | 6 out |
| Saturday, August 29 |
| » Defeated Phillies (54-77), 11-1 | Forbes Field (42-28) | 68-62 | Won 3 |
| » Starters: Robin Roberts vs Bob Friend | Third | 5½ out |
| Sunday, August 30 |
| » Defeated Phillies (54-78), 2-1 | Forbes Field (43-28) | 69-62 | Won 4 |
| » Starters: Humberto Robinson vs Harvey Haddix | Fourth | 4 out |
| » Defeated Phillies (54-79), 7-6 | Forbes Field (44-28) | 70-62 | Won 5 |
| » Starters: Ray Semproch vs Bennie Daniels | Fourth | 4 out |
| Wednesday, September 2 |
| » Lost to Reds (64-68), 6-3 | Crosley Field (3-5) | 70-63 | |
| » Starters: Vern Law vs Jim O'Toole | Fourth | 5 out |
| » Lost to Reds (65-68), 2-1 | Crosley Field (3-6) | 70-64 | Lost 2 |
| » Starters: Bob Friend vs Don Newcombe | Fourth | 5 out |
| Friday, September 4 |
| » Lost to Phillies (57-79), 3-0 | Shibe Park (5-4) | 70-65 | Lost 3 |
| » Starters: Harvey Haddix vs Jim Owens | Fourth | 5½ out |
| Saturday, September 5 |
| » Defeated Phillies (57-80), 7-6 | Shibe Park (6-4) | 71-65 | |
| » Starters: Ron Kline vs Don Cardwell | Fourth | 5½ out |
| Sunday, September 6 |
| » Lost to Phillies (58-80), 2-1 | Shibe Park (6-5) | 71-66 | |
| » Starters: Vern Law vs Robin Roberts | Fourth | 5½ out |
| Monday, September 7 |
| » Lost to Braves (73-63), 5-1 | County Stadium (2-8) | 71-67 | Lost 2 |
| » Starters: Bob Friend vs Lew Burdette | Third | 7 out |
| » Lost to Braves (74-63), 4-1 | County Stadium (2-9) | 71-68 | Lost 3 |
| » Starters: Bennie Daniels vs Bob Buhl | Third | 7 out |
| Wednesday, September 9 |
| » Lost to Giants (78-60), 7-2 | Seals Stadium (3-7) | 71-69 | Lost 4 |
| » Starters: Harvey Haddix vs Jack Sanford | Third | 8 out |
| Future Pirate Tom Foley is born in Columbus, GA. |
| Thursday, September 10 |
| » Defeated Giants (78-61), 5-3 | Seals Stadium (4-7) | 72-69 | |
| » Starters: Vern Law vs Johnny Antonelli | Third | 7 out |
| Friday, September 11 |
| » Lost to Dodgers (77-63), 5-4 | Los Angeles Memorial Coliseum (3-6) | 72-70 | |
| » Starters: Bob Friend vs Sandy Koufax | Fourth | 7½ out |
| » Lost to Dodgers (78-63), 4-0 | Los Angeles Memorial Coliseum (3-7) | 72-71 | Lost 2 |
| » Starters: Fred Green vs Larry Sherry | Fourth | 7½ out |
| Sunday, September 13 |
| » Defeated Dodgers (78-64), 4-3 | Los Angeles Memorial Coliseum (4-7) | 73-71 | |
| » Starters: Ron Kline vs Johnny Podres | Third | 8 out |
| Wednesday, September 16 |
| » Defeated Cubs (68-75), 3-2 | Wrigley Field (6-4) | 74-71 | Won 2 |
| » Starters: Vern Law vs Bob Anderson | Fourth | 7½ out |
| » Lost to Cubs (69-75), 4-2 | Wrigley Field (6-5) | 74-72 | |
| » Starters: Bob Friend vs Ben Johnson | Fourth | 7½ out |
| Thursday, September 17 |
| » Defeated Cardinals (66-80), 7-0 | Sportsman's Park III (6-5) | 75-72 | |
| » Starters: Harvey Haddix vs Larry Jackson | Third | 7½ out |
| Saturday, September 19 |
| » Defeated Reds (72-77), 4-3 | Forbes Field (45-28) | 76-72 | Won 2 |
| » Starters: Don Newcombe vs Dick Hall | Third | 6 out |
| Sunday, September 20 |
| » Defeated Reds (72-78), 10-1 | Forbes Field (46-28) | 77-72 | Won 3 |
| » Starters: Jim Brosnan vs Vern Law | Fourth | 6 out |
| Monday, September 21 |
| » Lost to Braves (83-66), 8-6 | Forbes Field (46-29) | 77-73 | |
| » Starters: Warren Spahn vs Bob Friend | Third | 6½ out |
| Future Pirate Danny Cox is born in Northampton, England. |
| Tuesday, September 22 |
| » Lost to Braves (84-66), 5-3 | Forbes Field (46-30) | 77-74 | Lost 2 |
| » Starters: Juan Pizarro vs Harvey Haddix | Fourth | 7½ out |
| Future Pirate Wally Backman is born in Hillsboro, OR. |
| Wednesday, September 23 |
| » Defeated Braves (84-67), 5-4 | Forbes Field (47-30) | 78-74 | |
| » Starters: Bob Buhl vs Ron Kline | Third | 6½ out |
| Future Pirate Jim Winn is born in Stockton, CA. |
| Saturday, September 26 |
| » Lost to Reds (73-80), 7-6 | Crosley Field (3-7) | 78-75 | |
| » Starters: Jim Umbricht vs Jim O'Toole | Third | 7 out |
| » Major-league debuts: Jim Umbricht (Pirates) |
| Sunday, September 27 |
| » Lost to Reds (74-80), 9-7 | Crosley Field (3-8) | 78-76 | Lost 2 |
| » Starters: Al Jackson vs Jay Hook | Third | 8 out |
| Friday, October 9 |
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