| Saturday, January 14 |
| Future Pirate Joe Redfield is born in Doylestown, PA. |
| Saturday, January 28 |
| Former Pirate Red Oldham dies in Costa Mesa, CA at the age of 68. |
| Thursday, February 16 |
| Former Pirate Dazzy Vance dies in Homosassa Springs, FL at the age of 70. |
| Friday, February 17 |
| Former Pirate Doc Johnston dies in Chattanooga, TN at the age of 74. |
| Monday, February 20 |
| Former Pirate Otto Krueger dies in St.Louis, MO at the age of 85. |
| Thursday, February 23 |
| Future Pirate Mike Smith is born in Jackson, MS. |
| Friday, March 3 |
| Future Pirate Ron Wotus is born in Colchester, CT. |
| Wednesday, March 29 |
| Future Pirate Mike Kingery is born in St. James, MN. |
| Saturday, April 8 |
| Former Pirate Fred Brickell dies in Wichita, KS at the age of 55. |
| Tuesday, April 11 |
| » Defeated Giants (0-1), 8-7 | Candlestick Park (1-0) | 1-0 | |
| » Starters: Bob Friend vs Sam Jones | First | -- |
| » Major-league debuts: Tom Haller and Chuck Hiller (Giants) |
| Wednesday, April 12 |
| » Lost to Giants (1-1), 2-1 | Candlestick Park (1-1) | 1-1 | |
| » Starters: Vern Law vs Billy Loes | Third | 1 out |
| » Major-league debuts: Jim Duffalo (Giants) |
| Thursday, April 13 |
| » Lost to Giants (2-1), 6-5 | Candlestick Park (1-2) | 1-2 | Lost 2 |
| » Starters: Harvey Haddix vs Jack Sanford | Fourth | 1½ out |
| Friday, April 14 |
| » Defeated Dodgers (2-2), 6-3 | Los Angeles Memorial Coliseum (1-0) | 2-2 | |
| » Starters: Joe Gibbon vs Sandy Koufax | Third | 1½ out |
| » Major-league debuts: Ron Perranoski (Dodgers) |
| Former Pirate Cy Falkenberg dies in San Francisco, CA at the age of 81. |
| Saturday, April 15 |
| » Defeated Dodgers (2-3), 4-1 | Los Angeles Memorial Coliseum (2-0) | 3-2 | Won 2 |
| » Starters: Bob Friend vs Don Drysdale | Second | ½ out |
| Sunday, April 16 |
| » Lost to Dodgers (3-3), 13-6 | Los Angeles Memorial Coliseum (2-1) | 3-3 | |
| » Starters: Vern Law vs Stan Williams | Fourth | 1 out |
| Tuesday, April 18 |
| » Defeated Cubs (2-3), 5-3 | Forbes Field (1-0) | 4-3 | |
| » Starters: Dick Ellsworth vs Vinegar Bend Mizell | Second | ½ out |
| Wednesday, April 19 |
| » Defeated Cubs (2-4), 4-1 | Forbes Field (2-0) | 5-3 | Won 2 |
| » Starters: Bob Anderson vs Bob Friend | Second | ½ out |
| Thursday, April 20 |
| » Lost to Cubs (3-4), 3-0 | Forbes Field (2-1) | 5-4 | |
| » Starters: Glen Hobbie vs Joe Gibbon | Second | ½ out |
| Saturday, April 22 |
| » Major-league debuts: Jack Curtis (Cubs) |
| Sunday, April 23 |
| » Lost to Braves (3-3), 3-1 | Forbes Field (2-2) | 5-5 | Lost 2 |
| » Starters: Warren Spahn vs Vern Law | Fourth | 1½ out |
| Monday, April 24 |
| » Defeated Braves (3-4), 7-6 | Forbes Field (3-2) | 6-5 | |
| » Starters: Bob Buhl vs Bob Friend | Second | 1 out |
| Wednesday, April 26 |
| » Defeated Phillies (4-8), 3-2 | Forbes Field (4-2) | 7-5 | Won 2 |
| » Starters: Dallas Green vs Vinegar Bend Mizell | Second | ½ out |
| Future Pirate Curtis Wilkerson is born in Petersburg, VA. |
| Saturday, April 29 |
| » Defeated Reds (5-9), 6-3 | Crosley Field (1-0) | 8-5 | Won 3 |
| » Starters: Vern Law vs Joey Jay | First | -- |
| Sunday, April 30 |
| » Defeated Reds (5-10), 6-3 | Crosley Field (2-0) | 9-5 | Won 4 |
| » Starters: Bob Friend vs Jay Hook | Second | ½ out |
| » Lost to Reds (6-10), 4-2 | Crosley Field (2-1) | 9-6 | |
| » Starters: Joe Gibbon vs Bob Purkey | Second | ½ out |
| Tuesday, May 2 |
| » Defeated Cardinals (7-10), 6-0 | Sportsman's Park III (1-0) | 10-6 | |
| » Starters: Harvey Haddix vs Ernie Broglio | First | -- |
| Wednesday, May 3 |
| » Lost to Cardinals (8-10), 3-1 | Sportsman's Park III (1-1) | 10-7 | |
| » Starters: Vinegar Bend Mizell vs Bob Gibson | Second | ½ out |
| Friday, May 5 |
| » Lost to Dodgers (12-10), 10-0 | Forbes Field (4-3) | 10-8 | Lost 2 |
| » Starters: Johnny Podres vs Bob Friend | Second | 2 out |
| Saturday, May 6 |
| » Defeated Dodgers (12-11), 9-5 | Forbes Field (5-3) | 11-8 | |
| » Starters: Roger Craig vs Joe Gibbon | Second | 1½ out |
| Sunday, May 7 |
| » Lost to Dodgers (13-11), 4-2 | Forbes Field (5-4) | 11-9 | |
| » Starters: Sandy Koufax vs George Witt | Third | 2½ out |
| Tuesday, May 9 |
| » Defeated Giants (14-8), 9-6 | Forbes Field (6-4) | 12-9 | |
| » Starters: Jack Sanford vs Harvey Haddix | Third | 1½ out |
| Wednesday, May 10 |
| » Lost to Giants (15-8), 3-0 | Forbes Field (6-5) | 12-10 | |
| » Starters: Mike McCormick vs Bob Friend | Fourth | 2½ out |
| Friday, May 12 |
| » Defeated Reds (14-11), 8-5 | Forbes Field (7-5) | 13-10 | |
| » Starters: Bob Purkey vs Vinegar Bend Mizell | Third | 1½ out |
| Saturday, May 13 |
| » Defeated Reds (14-12), 13-5 | Forbes Field (8-5) | 14-10 | Won 2 |
| » Starters: Jim O'Toole vs Joe Gibbon | Third | 1½ out |
| Sunday, May 14 |
| » Lost to Reds (15-12), 4-1 | Forbes Field (8-6) | 14-11 | |
| » Starters: Ken Hunt vs Bob Friend | Third | 2½ out |
| Tuesday, May 16 |
| » Defeated Cardinals (11-14), 2-1 | Forbes Field (9-6) | 15-11 | |
| » Starters: Curt Simmons vs Vern Law | Second | 3 out |
| Wednesday, May 17 |
| » Defeated Cardinals (11-15), 4-3 | Forbes Field (10-6) | 16-11 | Won 2 |
| » Starters: Ernie Broglio vs Vinegar Bend Mizell | Second | 3 out |
| Former Pirate Otto Knabe dies in Philadelphia, PA at the age of 77. |
| Friday, May 19 |
| » Lost to Phillies (9-21), 4-1 | Shibe Park (0-1) | 16-12 | |
| » Starters: Bob Friend vs Art Mahaffey | Fourth | 3 out |
| Saturday, May 20 |
| » Defeated Phillies (9-22), 4-3 | Shibe Park (1-1) | 17-12 | |
| » Starters: Joe Gibbon vs Robin Roberts | Third | 2 out |
| Sunday, May 21 |
| » Defeated Phillies (9-23), 13-11 | Shibe Park (2-1) | 18-12 | Won 2 |
| » Starters: Vern Law vs Dallas Green | Third | 1 out |
| Monday, May 22 |
| » Defeated Braves (15-16), 2-1 | County Stadium (1-0) | 19-12 | Won 3 |
| » Starters: Harvey Haddix vs Bob Buhl | Third | 1 out |
| Tuesday, May 23 |
| » Lost to Braves (16-16), 1-0 | County Stadium (1-1) | 19-13 | |
| » Starters: Bobby Shantz vs Lew Burdette | Third | 1 out |
| Wednesday, May 24 |
| » Defeated Cubs (12-23), 7-3 | Wrigley Field (1-0) | 20-13 | |
| » Starters: Vinegar Bend Mizell vs Dick Ellsworth | Second | 1 out |
| Friday, May 26 |
| » Lost to Cardinals (16-19), 12-2 | Sportsman's Park III (1-2) | 20-14 | |
| » Starters: Bob Friend vs Curt Simmons | Second | 2 out |
| Saturday, May 27 |
| » Lost to Cardinals (17-19), 7-5 | Sportsman's Park III (1-3) | 20-15 | Lost 2 |
| » Starters: Vern Law vs Ernie Broglio | Third | 3 out |
| Sunday, May 28 |
| » Lost to Cardinals (18-19), 8-4 | Sportsman's Park III (1-4) | 20-16 | Lost 3 |
| » Starters: Harvey Haddix vs Ray Sadecki | Fourth | 4 out |
| Tuesday, May 30 |
| » Lost to Cubs (13-26), 5-3 | Forbes Field (10-7) | 20-17 | Lost 4 |
| » Starters: Dick Ellsworth vs Vinegar Bend Mizell | Third | 3½ out |
| » Lost to Cubs (14-26), 10-0 | Forbes Field (10-8) | 20-18 | Lost 5 |
| » Starters: Don Cardwell vs Bob Friend | Third | 3½ out |
| Wednesday, May 31 |
| » Defeated Braves (19-20), 9-1 | Forbes Field (11-8) | 21-18 | |
| » Starters: Warren Spahn vs Joe Gibbon | Third | 3½ out |
| Thursday, June 1 |
| » Defeated Braves (19-21), 8-2 | Forbes Field (12-8) | 22-18 | Won 2 |
| » Starters: Lew Burdette vs Harvey Haddix | Fourth | 3 out |
| Friday, June 2 |
| » Lost to Phillies (13-28), 6-0 | Forbes Field (12-9) | 22-19 | |
| » Starters: John Buzhardt vs Bob Friend | Fourth | 3 out |
| Future Pirate Jeff Schulz is born in Evansville, IN. |
| Saturday, June 3 |
| » Defeated Phillies (13-29), 5-1 | Forbes Field (13-9) | 23-19 | |
| » Starters: Art Mahaffey vs Bobby Shantz | Fourth | 3 out |
| Sunday, June 4 |
| » Lost to Phillies (14-29), 5-0 | Forbes Field (13-10) | 23-20 | |
| » Starters: Don Ferrarese vs Vinegar Bend Mizell | Third | 3 out |
| Monday, June 5 |
| » Defeated Dodgers (29-21), 5-2 | Los Angeles Memorial Coliseum (3-1) | 24-20 | |
| » Starters: Vern Law vs Don Drysdale | Fourth | 2½ out |
| Former Pirate Syd Smith dies in Orangeburg, SC at the age of 78. |
| Tuesday, June 6 |
| » Lost to Dodgers (30-21), 8-7 | Los Angeles Memorial Coliseum (3-2) | 24-21 | |
| » Starters: Joe Gibbon vs Roger Craig | Fourth | 3½ out |
| Wednesday, June 7 |
| » Lost to Dodgers (31-21), 7-3 | Los Angeles Memorial Coliseum (3-3) | 24-22 | Lost 2 |
| » Starters: Earl Francis vs Sandy Koufax | Fourth | 4 out |
| Thursday, June 8 |
| » Defeated Dodgers (31-22), 4-2 | Los Angeles Memorial Coliseum (4-3) | 25-22 | |
| » Starters: Bob Friend vs Stan Williams | Fourth | 3½ out |
| Friday, June 9 |
| » Lost to Giants (29-22), 9-6 | Candlestick Park (1-3) | 25-23 | |
| » Starters: Harvey Haddix vs Juan Marichal | Fourth | 4 out |
| Saturday, June 10 |
| » Lost to Giants (30-22), 5-0 | Candlestick Park (1-4) | 25-24 | Lost 2 |
| » Starters: Vinegar Bend Mizell vs Mike McCormick | Fourth | 5 out |
| Sunday, June 11 |
| » Defeated Giants (30-23), 8-4 | Candlestick Park (2-4) | 26-24 | |
| » Starters: Vern Law vs Billy Loes | Fourth | 5 out |
| Tuesday, June 13 |
| » Defeated Reds (33-22), 2-1 | Forbes Field (14-10) | 27-24 | Won 2 |
| » Starters: Jim Maloney vs Joe Gibbon | Fourth | 4 out |
| Wednesday, June 14 |
| » Defeated Reds (33-23), 5-4 | Forbes Field (15-10) | 28-24 | Won 3 |
| » Starters: Jim O'Toole vs Bob Friend | Third | 3½ out |
| Thursday, June 15 |
| » Lost to Reds (34-23), 8-1 | Forbes Field (15-11) | 28-25 | |
| » Starters: Joey Jay vs Vinegar Bend Mizell | Third | 4½ out |
| Friday, June 16 |
| » Lost to Cardinals (26-28), 5-2 | Forbes Field (15-12) | 28-26 | Lost 2 |
| » Starters: Bob Gibson vs Harvey Haddix | Fourth | 5 out |
| Saturday, June 17 |
| » Defeated Cardinals (26-29), 9-3 | Forbes Field (16-12) | 29-26 | |
| » Starters: Ernie Broglio vs Bobby Shantz | Fourth | 5 out |
| Sunday, June 18 |
| » Defeated Cardinals (26-30), 5-3 | Forbes Field (17-12) | 30-26 | Won 2 |
| » Starters: Curt Simmons vs Bob Friend | Fourth | 6 out |
| » Lost to Cardinals (27-30), 7-3 | Forbes Field (17-13) | 30-27 | |
| » Starters: Larry Jackson vs Joe Gibbon | Fourth | 6 out |
| Tuesday, June 20 |
| » Defeated Phillies (18-39), 6-2 | Shibe Park (3-1) | 31-27 | |
| » Starters: Harvey Haddix vs Art Mahaffey | Fourth | 5½ out |
| Future Pirate Gary Varsho is born in Marshfield, WI. |
| Thursday, June 22 |
| » Defeated Phillies (18-40), 5-1 | Shibe Park (4-1) | 32-27 | Won 2 |
| » Starters: Bob Friend vs John Buzhardt | Fourth | 6 out |
| Friday, June 23 |
| » Lost to Phillies (19-40), 12-11 | Forbes Field (17-14) | 32-28 | |
| » Starters: Robin Roberts vs Joe Gibbon | Fourth | 7 out |
| Saturday, June 24 |
| » Lost to Phillies (20-40), 6-2 | Forbes Field (17-15) | 32-29 | Lost 2 |
| » Starters: Chris Short vs Vinegar Bend Mizell | Fourth | 7 out |
| Sunday, June 25 |
| » Defeated Phillies (20-41), 10-5 | Forbes Field (18-15) | 33-29 | |
| » Starters: Don Ferrarese vs Bobby Shantz | Fourth | 7½ out |
| » Lost to Phillies (21-41), 4-3 | Forbes Field (18-16) | 33-30 | |
| » Starters: Art Mahaffey vs Harvey Haddix | Fourth | 7½ out |
| Tuesday, June 27 |
| » Lost to Dodgers (42-29), 9-5 | Forbes Field (18-17) | 33-31 | Lost 2 |
| » Starters: Johnny Podres vs Bob Friend | Fourth | 8½ out |
| Wednesday, June 28 |
| » Defeated Dodgers (42-30), 9-3 | Forbes Field (19-17) | 34-31 | |
| » Starters: Don Drysdale vs Joe Gibbon | Fourth | 7 out |
| Thursday, June 29 |
| » Defeated Dodgers (42-31), 4-2 | Forbes Field (20-17) | 35-31 | Won 2 |
| » Starters: Sandy Koufax vs Earl Francis | Fourth | 6 out |
| Friday, June 30 |
| » Defeated Giants (41-31), 4-3 | Forbes Field (21-17) | 36-31 | Won 3 |
| » Starters: Mike McCormick vs Harvey Haddix | Fourth | 6 out |
| Saturday, July 1 |
| » Lost to Giants (42-31), 4-3 | Forbes Field (21-18) | 36-32 | |
| » Starters: Jack Sanford vs Bob Friend | Fourth | 6 out |
| Sunday, July 2 |
| » Defeated Giants (42-32), 7-6 | Forbes Field (22-18) | 37-32 | |
| » Starters: Dick LeMay vs Vern Law | Fourth | 6 out |
| » Defeated Giants (42-33), 9-0 | Forbes Field (23-18) | 38-32 | Won 2 |
| » Starters: Juan Marichal vs Bobby Shantz | Fourth | 6 out |
| » Major-league debuts: Al McBean (Pirates) |
| Monday, July 3 |
| » Lost to Reds (48-29), 4-3 | Crosley Field (2-2) | 38-33 | |
| » Starters: Joe Gibbon vs Jim Maloney | Fourth | 7 out |
| Tuesday, July 4 |
| » Lost to Reds (49-29), 2-0 | Crosley Field (2-3) | 38-34 | Lost 2 |
| » Starters: Earl Francis vs Joey Jay | Fourth | 8 out |
| Thursday, July 6 |
| » Defeated Cubs (31-44), 15-3 | Wrigley Field (2-0) | 39-34 | |
| » Starters: Bob Friend vs Dick Ellsworth | Fourth | 9 out |
| » Lost to Cubs (32-44), 5-1 | Wrigley Field (2-1) | 39-35 | |
| » Starters: Vinegar Bend Mizell vs Glen Hobbie | Fourth | 9 out |
| Friday, July 7 |
| » Defeated Braves (37-38), 6-5 | County Stadium (2-1) | 40-35 | |
| » Starters: Harvey Haddix vs Tony Cloninger | Fourth | 9½ out |
| Saturday, July 8 |
| » Defeated Braves (37-39), 4-3 | County Stadium (3-1) | 41-35 | Won 2 |
| » Starters: Joe Gibbon vs Bob Buhl | Third | 8½ out |
| Sunday, July 9 |
| » Defeated Braves (37-40), 5-4 | County Stadium (4-1) | 42-35 | Won 3 |
| » Starters: Clem Labine vs Lew Burdette | Third | 8½ out |
| Thursday, July 13 |
| » Lost to Giants (45-39), 2-1 | Candlestick Park (2-5) | 42-36 | |
| » Starters: Bob Friend vs Billy O'Dell | Third | 9½ out |
| Friday, July 14 |
| » Defeated Giants (45-40), 6-4 | Candlestick Park (3-5) | 43-36 | |
| » Starters: Joe Gibbon vs Jack Sanford | Third | 8½ out |
| » Major-league debuts: John Orsino (Giants) |
| Saturday, July 15 |
| » Lost to Giants (46-40), 8-3 | Candlestick Park (3-6) | 43-37 | |
| » Starters: Harvey Haddix vs Mike McCormick | Third | 9½ out |
| Sunday, July 16 |
| » Lost to Dodgers (51-37), 12-11 | Los Angeles Memorial Coliseum (4-4) | 43-38 | Lost 2 |
| » Starters: Earl Francis vs Ron Perranoski | Fourth | 9½ out |
| Former Pirate Mike Mitchell dies in Phoenix, AZ at the age of 82. |
| Monday, July 17 |
| » Lost to Dodgers (52-37), 6-4 | Los Angeles Memorial Coliseum (4-5) | 43-39 | Lost 3 |
| » Starters: Bob Friend vs Stan Williams | Fourth | 9½ out |
| Thursday, July 20 |
| » Defeated Cubs (38-51), 4-0 | Forbes Field (24-18) | 44-39 | |
| » Starters: Jack Curtis vs Joe Gibbon | Fourth | 7½ out |
| Friday, July 21 |
| » Lost to Braves (44-43), 5-3 | Forbes Field (24-19) | 44-40 | |
| » Starters: Lew Burdette vs Bob Friend | Fourth | 8 out |
| Saturday, July 22 |
| » Lost to Braves (45-43), 5-4 | Forbes Field (24-20) | 44-41 | Lost 2 |
| » Starters: Warren Spahn vs Bobby Shantz | Fourth | 8 out |
| Sunday, July 23 |
| » Lost to Braves (46-43), 11-4 | Forbes Field (24-21) | 44-42 | Lost 3 |
| » Starters: Bob Buhl vs Harvey Haddix | Fifth | 10 out |
| » Lost to Braves (47-43), 5-4 | Forbes Field (24-22) | 44-43 | Lost 4 |
| » Starters: Carl Willey vs Earl Francis | Fifth | 10 out |
| Tuesday, July 25 |
| » Lost to Giants (50-44), 16-7 | Forbes Field (24-23) | 44-44 | Lost 5 |
| » Starters: Mike McCormick vs Joe Gibbon | Fifth | 10½ out |
| Wednesday, July 26 |
| » Defeated Giants (50-45), 8-3 | Forbes Field (25-23) | 45-44 | |
| » Starters: Jack Sanford vs Bob Friend | Fifth | 10½ out |
| Thursday, July 27 |
| » Lost to Giants (51-45), 2-0 | Forbes Field (25-24) | 45-45 | |
| » Starters: Juan Marichal vs Vinegar Bend Mizell | Fifth | 11½ out |
| Friday, July 28 |
| » Lost to Dodgers (60-38), 6-4 | Forbes Field (25-25) | 45-46 | Lost 2 |
| » Starters: Johnny Podres vs Earl Francis | Fifth | 12½ out |
| Saturday, July 29 |
| » Lost to Dodgers (61-38), 5-4 | Forbes Field (25-26) | 45-47 | Lost 3 |
| » Starters: Sandy Koufax vs Harvey Haddix | Fifth | 12½ out |
| Sunday, July 30 |
| » Lost to Dodgers (62-38), 7-3 | Forbes Field (25-27) | 45-48 | Lost 4 |
| » Starters: Don Drysdale vs Joe Gibbon | Fifth | 13½ out |
| Wednesday, August 2 |
| » Lost to Cardinals (48-52), 4-2 | Sportsman's Park III (1-5) | 45-49 | Lost 5 |
| » Starters: Bob Friend vs Larry Jackson | Sixth | 14½ out |
| Thursday, August 3 |
| » Defeated Cardinals (48-53), 19-0 | Sportsman's Park III (2-5) | 46-49 | |
| » Starters: Harvey Haddix vs Al Cicotte | Fifth | 14½ out |
| Friday, August 4 |
| » Lost to Reds (67-40), 5-4 | Crosley Field (2-4) | 46-50 | |
| » Starters: Joe Gibbon vs Bob Purkey | Sixth | 15½ out |
| Saturday, August 5 |
| » Defeated Reds (67-41), 11-7 | Crosley Field (3-4) | 47-50 | |
| » Starters: Tom Sturdivant vs Ken Hunt | Fifth | 14½ out |
| Sunday, August 6 |
| » Defeated Reds (67-42), 9-4 | Crosley Field (4-4) | 48-50 | Won 2 |
| » Starters: Vinegar Bend Mizell vs Joey Jay | Sixth | 14 out |
| » Lost to Reds (68-42), 3-2 | Crosley Field (4-5) | 48-51 | |
| » Starters: Earl Francis vs Jim O'Toole | Sixth | 14 out |
| Monday, August 7 |
| » Defeated Phillies (30-74), 3-1 | Shibe Park (5-1) | 49-51 | |
| » Starters: Bob Friend vs John Buzhardt | Sixth | 13½ out |
| Tuesday, August 8 |
| » Defeated Phillies (30-75), 10-2 | Shibe Park (6-1) | 50-51 | Won 2 |
| » Starters: Harvey Haddix vs Art Mahaffey | Sixth | 13 out |
| » Defeated Phillies (30-76), 3-2 | Shibe Park (7-1) | 51-51 | Won 3 |
| » Starters: Tom Sturdivant vs Chris Short | Sixth | 13 out |
| Wednesday, August 9 |
| » Lost to Cardinals (55-53), 4-0 | Forbes Field (25-28) | 51-52 | |
| » Starters: Curt Simmons vs Joe Gibbon | Sixth | 14 out |
| Thursday, August 10 |
| » Lost to Cardinals (56-53), 3-2 | Forbes Field (25-29) | 51-53 | Lost 2 |
| » Starters: Ray Sadecki vs Earl Francis | Sixth | 14½ out |
| Friday, August 11 |
| » Defeated Phillies (30-78), 6-0 | Forbes Field (26-29) | 52-53 | |
| » Starters: Robin Roberts vs Bob Friend | Sixth | 14 out |
| Saturday, August 12 |
| » Defeated Phillies (30-79), 4-0 | Forbes Field (27-29) | 53-53 | Won 2 |
| » Starters: Jim Owens vs Vinegar Bend Mizell | Sixth | 14 out |
| Sunday, August 13 |
| » Defeated Phillies (30-80), 13-4 | Forbes Field (28-29) | 54-53 | Won 3 |
| » Starters: John Buzhardt vs Tom Sturdivant | Sixth | 14 out |
| Monday, August 14 |
| » Lost to Braves (58-51), 8-3 | County Stadium (4-2) | 54-54 | |
| » Starters: Harvey Haddix vs Bob Buhl | Sixth | 14 out |
| Tuesday, August 15 |
| » Lost to Braves (59-51), 4-1 | County Stadium (4-3) | 54-55 | Lost 2 |
| » Starters: Joe Gibbon vs Carl Willey | Sixth | 14 out |
| Wednesday, August 16 |
| » Lost to Braves (60-51), 2-1 | County Stadium (4-4) | 54-56 | Lost 3 |
| » Starters: Bob Friend vs Warren Spahn | Sixth | 14½ out |
| Thursday, August 17 |
| » Lost to Cubs (48-65), 11-4 | Wrigley Field (2-2) | 54-57 | Lost 4 |
| » Starters: Vinegar Bend Mizell vs Glen Hobbie | Sixth | 14½ out |
| » Defeated Cubs (48-66), 4-3 | Wrigley Field (3-2) | 55-57 | |
| » Starters: Earl Francis vs Jim Brewer | Sixth | 14½ out |
| Friday, August 18 |
| » Lost to Cubs (49-66), 2-1 | Wrigley Field (3-3) | 55-58 | |
| » Starters: Tom Sturdivant vs Dick Ellsworth | Sixth | 15½ out |
| Saturday, August 19 |
| » Defeated Cubs (49-67), 4-3 | Wrigley Field (4-3) | 56-58 | |
| » Starters: Harvey Haddix vs Jack Curtis | Sixth | 15½ out |
| Sunday, August 20 |
| » Lost to Cubs (50-67), 1-0 | Wrigley Field (4-4) | 56-59 | |
| » Starters: Bob Friend vs Don Cardwell | Sixth | 15½ out |
| Tuesday, August 22 |
| » Defeated Braves (64-53), 4-1 | Forbes Field (29-29) | 57-59 | |
| » Starters: Bob Buhl vs Joe Gibbon | Sixth | 14 out |
| Wednesday, August 23 |
| » Defeated Braves (64-54), 7-6 | Forbes Field (30-29) | 58-59 | Won 2 |
| » Starters: Lew Burdette vs Earl Francis | Sixth | 13 out |
| Thursday, August 24 |
| » Lost to Braves (65-54), 6-1 | Forbes Field (30-30) | 58-60 | |
| » Starters: Warren Spahn vs Bob Friend | Sixth | 14 out |
| Friday, August 25 |
| » Defeated Cubs (50-70), 1-0 | Forbes Field (31-30) | 59-60 | |
| » Starters: Don Cardwell vs Tom Sturdivant | Sixth | 13 out |
| Saturday, August 26 |
| » Lost to Cubs (51-70), 7-3 | Forbes Field (31-31) | 59-61 | |
| » Starters: Dick Ellsworth vs Harvey Haddix | Sixth | 13 out |
| Sunday, August 27 |
| » Defeated Cubs (51-71), 7-3 | Forbes Field (32-31) | 60-61 | |
| » Starters: Jack Curtis vs Joe Gibbon | Sixth | 14 out |
| » Lost to Cubs (52-71), 6-5 | Forbes Field (32-32) | 60-62 | |
| » Starters: Jim Brewer vs Vinegar Bend Mizell | Sixth | 14 out |
| Future Pirate Mike Maddux is born in Dayton, OH. |
| Monday, August 28 |
| » Lost to Cubs (53-71), 5-4 | Forbes Field (32-33) | 60-63 | Lost 2 |
| » Starters: Dick Drott vs Earl Francis | Sixth | 14½ out |
| Tuesday, August 29 |
| » Lost to Reds (79-52), 3-0 | Forbes Field (32-34) | 60-64 | Lost 3 |
| » Starters: Jim O'Toole vs Bob Friend | Sixth | 15½ out |
| Wednesday, August 30 |
| » Defeated Reds (79-53), 3-1 | Forbes Field (33-34) | 61-64 | |
| » Starters: Bob Purkey vs Tom Sturdivant | Sixth | 14½ out |
| Friday, September 1 |
| » Lost to Cardinals (68-61), 8-4 | Sportsman's Park III (2-6) | 61-65 | |
| » Starters: Joe Gibbon vs Larry Jackson | Sixth | 15 out |
| Saturday, September 2 |
| » Defeated Cardinals (68-62), 5-4 | Sportsman's Park III (3-6) | 62-65 | |
| » Starters: Harvey Haddix vs Ernie Broglio | Sixth | 15 out |
| Sunday, September 3 |
| » Defeated Cardinals (68-63), 8-1 | Sportsman's Park III (4-6) | 63-65 | Won 2 |
| » Starters: Bob Friend vs Curt Simmons | Sixth | 14 out |
| Monday, September 4 |
| » Lost to Cardinals (69-63), 9-4 | Sportsman's Park III (4-7) | 63-66 | |
| » Starters: Earl Francis vs Ray Sadecki | Sixth | 14½ out |
| Tuesday, September 5 |
| » Defeated Cubs (57-76), 8-3 | Wrigley Field (5-4) | 64-66 | |
| » Starters: Tom Sturdivant vs Glen Hobbie | Sixth | 14½ out |
| Wednesday, September 6 |
| » Lost to Cubs (58-76), 6-2 | Wrigley Field (5-5) | 64-67 | |
| » Starters: Joe Gibbon vs Don Cardwell | Sixth | 14½ out |
| Thursday, September 7 |
| » Defeated Cubs (58-77), 7-5 | Wrigley Field (6-5) | 65-67 | |
| » Starters: Harvey Haddix vs Jim Brewer | Sixth | 14 out |
| Friday, September 8 |
| » Defeated Braves (74-61), 2-1 | County Stadium (5-4) | 66-67 | Won 2 |
| » Starters: Bob Friend vs Bob Hendley | Sixth | 14 out |
| Saturday, September 9 |
| » Lost to Braves (75-61), 4-3 | County Stadium (5-5) | 66-68 | |
| » Starters: Earl Francis vs Carl Willey | Sixth | 15 out |
| Sunday, September 10 |
| » Lost to Braves (76-61), 4-3 | County Stadium (5-6) | 66-69 | Lost 2 |
| » Starters: Tom Sturdivant vs Warren Spahn | Sixth | 16 out |
| Monday, September 11 |
| » Lost to Giants (74-62), 4-3 | Candlestick Park (3-7) | 66-70 | Lost 3 |
| » Starters: Al McBean vs Jack Sanford | Sixth | 16½ out |
| Tuesday, September 12 |
| » Defeated Giants (74-63), 3-0 | Candlestick Park (4-7) | 67-70 | |
| » Starters: Joe Gibbon vs Mike McCormick | Sixth | 16½ out |
| Wednesday, September 13 |
| » Defeated Dodgers (79-59), 8-2 | Los Angeles Memorial Coliseum (5-5) | 68-70 | Won 2 |
| » Starters: Bob Friend vs Don Drysdale | Sixth | 16½ out |
| Thursday, September 14 |
| » Lost to Dodgers (80-59), 7-6 | Los Angeles Memorial Coliseum (5-6) | 68-71 | |
| » Starters: Tom Sturdivant vs Stan Williams | Sixth | 17 out |
| Saturday, September 16 |
| » Lost to Cardinals (75-67), 6-3 | Forbes Field (33-35) | 68-72 | Lost 2 |
| » Starters: Ray Sadecki vs Earl Francis | Sixth | 18 out |
| Future Pirate Scott Medvin is born in North Olmsted, OH. Future Pirate Mark Parent is born in Ashland, OR. |
| Sunday, September 17 |
| » Lost to Cardinals (76-67), 3-0 | Forbes Field (33-36) | 68-73 | Lost 3 |
| » Starters: Larry Jackson vs Al McBean | Fifth | 18 out |
| Monday, September 18 |
| » Defeated Cardinals (76-68), 8-6 | Forbes Field (34-36) | 69-73 | |
| » Starters: Bob Gibson vs Larry Foss | Fifth | 17½ out |
| » Major-league debuts: Larry Foss (Pirates) |
| Tuesday, September 19 |
| » Lost to Reds (89-57), 10-1 | Crosley Field (4-6) | 69-74 | |
| » Starters: Bob Friend vs Jim O'Toole | Sixth | 18½ out |
| Wednesday, September 20 |
| » Lost to Reds (90-57), 3-2 | Crosley Field (4-7) | 69-75 | Lost 2 |
| » Starters: Joe Gibbon vs Joey Jay | Fifth | 19½ out |
| Friday, September 22 |
| » Defeated Phillies (45-102), 6-3 | Shibe Park (8-1) | 70-75 | |
| » Starters: Tom Sturdivant vs Jim Owens | Sixth | 18½ out |
| » Major-league debuts: Donn Clendenon (Pirates) |
| Saturday, September 23 |
| » Lost to Phillies (46-102), 5-4 | Shibe Park (8-2) | 70-76 | |
| » Starters: Al Jackson vs John Buzhardt | Sixth | 19½ out |
| Sunday, September 24 |
| » Defeated Phillies (46-103), 4-3 | Shibe Park (9-2) | 71-76 | |
| » Starters: Larry Foss vs Dallas Green | Sixth | 18½ out |
| Tuesday, September 26 |
| » Lost to Dodgers (87-62), 5-3 | Forbes Field (34-37) | 71-77 | |
| » Starters: Stan Williams vs Bob Friend | Sixth | 19 out |
| » Defeated Dodgers (87-63), 8-0 | Forbes Field (35-37) | 72-77 | |
| » Starters: Don Drysdale vs Joe Gibbon | Sixth | 19 out |
| Future Pirate Steve Buechele is born in Lancaster, CA. |
| Wednesday, September 27 |
| » Defeated Giants (83-67), 5-3 | Forbes Field (36-37) | 73-77 | Won 2 |
| » Starters: Billy O'Dell vs Tom Sturdivant | Sixth | 18½ out |
| Thursday, September 28 |
| » Lost to Giants (84-67), 7-4 | Forbes Field (36-38) | 73-78 | |
| » Starters: Jim Duffalo vs Earl Francis | Sixth | 19 out |
| Friday, September 29 |
| » Lost to Reds (93-59), 8-1 | Forbes Field (36-39) | 73-79 | Lost 2 |
| » Starters: Jim O'Toole vs Larry Foss | Sixth | 20 out |
| Saturday, September |
