| D1 | 30/04/1960 | Leicester City | 1-2 | Bolton Wanderers | Deakin P 2 | | 19,527 | Win |
| D1 | 23/04/1960 | Bolton Wanderers | 2-0 | Chelsea | Hill, Birch | | 19,432 | Win |
| D1 | 18/04/1960 | Bolton Wanderers | 3-1 | Manchester City | Holden D, Stevens D, Birch | | 35,591 | Win |
| D1 | 16/04/1960 | Leeds United | 1-0 | Bolton Wanderers | | | 19,272 | Loss |
| D1 | 15/04/1960 | Manchester City | 1-0 | Bolton Wanderers | | | 50,053 | Loss |
| D1 | 09/04/1960 | Bolton Wanderers | 2-1 | Preston North End | Hartle (pen), Stevens D | | 30,816 | Win |
| D1 | 02/04/1960 | Manchester United | 2-0 | Bolton Wanderers | | | 45,482 | Loss |
| D1 | 26/03/1960 | Bolton Wanderers | 2-1 | Tottenham Hotspur | Holden D, Parry R | | 31,106 | Win |
| D1 | 19/03/1960 | Birmingham City | 2-5 | Bolton Wanderers | Stevens D, Hill 2, Bannister N, Hartle (pen) | | 24,183 | Win |
| D1 | 12/03/1960 | Bolton Wanderers | 1-4 | Newcastle United | Stevens D | | 24,648 | Loss |
| D1 | 09/03/1960 | Bolton Wanderers | 2-2 | Luton Town | Hill, Birch | | 14,791 | Draw |
| D1 | 05/03/1960 | West Bromwich Albion | 1-1 | Bolton Wanderers | Holden D | | 23,707 | Draw |
| D1 | 27/02/1960 | Bolton Wanderers | 2-1 | Burnley | Hartle, Birch | | 28,772 | Win |
| D1 | 24/02/1960 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | | 34,464 | Loss |
| D1 | 13/02/1960 | Bolton Wanderers | 1-1 | Nottingham Forest | Stanley G | | 16,218 | Draw |
| D1 | 06/02/1960 | Fulham | 1-1 | Bolton Wanderers | Birch | | 24,743 | Draw |
| FAC4 | 30/01/1960 | West Bromwich Albion | 2-0 | Bolton Wanderers | | | 36,207 | Loss |
| D1 | 23/01/1960 | West Ham United | 1-2 | Bolton Wanderers | Stevens D, Parry R | | 21,155 | Win |
| FAC3R | 14/01/1960 | Bolton Wanderers | 4-2 | Bury | Stevens D, Parry R 2, Birch (aet) | | 43,616 | Win |
| FAC3 | 09/01/1960 | Bury | 1-1 | Bolton Wanderers | Parry R | | 35,000 | Draw |
| D1 | 02/01/1960 | Everton | 0-1 | Bolton Wanderers | Stevens D | | 37,513 | Win |
| D1 | 28/12/1959 | Wolverhampton Wanderers | 0-1 | Bolton Wanderers | Birch | | 28,424 | Win |
| D1 | 26/12/1959 | Bolton Wanderers | 2-1 | Wolverhampton Wanderers | Hartle (pen), Stevens D | | 36,039 | Win |
| D1 | 19/12/1959 | Bolton Wanderers | 0-3 | Blackpool | | | 17,308 | Loss |
| D1 | 12/12/1959 | Bolton Wanderers | 4-1 | Birmingham City | Holden D, Stevens D, Parry R 2 | | 16,074 | Win |
| D1 | 05/12/1959 | Burnley | 4-0 | Bolton Wanderers | | | 26,510 | Loss |
| D1 | 28/11/1959 | Bolton Wanderers | 3-1 | Leicester City | Stevens D, Hartle (pen), Parry R | | 19,834 | Win |
| D1 | 21/11/1959 | Preston North End | 1-0 | Bolton Wanderers | | | 28,723 | Loss |
| D1 | 14/11/1959 | Bolton Wanderers | 1-1 | Manchester United | Stevens D | | 37,892 | Draw |
| D1 | 07/11/1959 | Tottenham Hotspur | 0-2 | Bolton Wanderers | Stevens D, Parry R | | 41,909 | Win |
| D1 | 31/10/1959 | Bolton Wanderers | 1-1 | Leeds United | Hennin | | 20,183 | Draw |
| D1 | 24/10/1959 | Newcastle United | 0-2 | Bolton Wanderers | Parry R 2 | | 34,679 | Win |
| D1 | 17/10/1959 | Bolton Wanderers | 0-0 | West Bromwich Albion | | | 22,581 | Draw |
| D1 | 10/10/1959 | Chelsea | 0-2 | Bolton Wanderers | Parry R, Hill | | 28,707 | Win |
| D1 | 03/10/1959 | Bolton Wanderers | 1-0 | Sheffield Wednesday | Parry R | | 23,990 | Win |
| D1 | 26/09/1959 | Nottingham Forest | 2-0 | Bolton Wanderers | | | 28,930 | Loss |
| D1 | 19/09/1959 | Bolton Wanderers | 3-2 | Fulham | Stevens D, Hill, Lampe (og) | | 24,751 | Win |
| D1 | 15/09/1959 | Arsenal | 2-1 | Bolton Wanderers | McCullough (og) | | 38,634 | Loss |
| D1 | 12/09/1959 | Bolton Wanderers | 5-1 | West Ham United | Banks T, Stevens D, Hill, Bannister N 2 | | 24,240 | Win |
| D1 | 09/09/1959 | Bolton Wanderers | 0-1 | Arsenal | | | 32,571 | Loss |
| D1 | 05/09/1959 | Luton Town | 0-0 | Bolton Wanderers | | | 15,604 | Draw |
| D1 | 31/08/1959 | Blackburn Rovers | 1-0 | Bolton Wanderers | | | 39,039 | Loss |
| D1 | 29/08/1959 | Bolton Wanderers | 2-1 | Everton | Stevens D, Parry R | | 26,792 | Win |
| D1 | 26/08/1959 | Bolton Wanderers | 0-3 | Blackburn Rovers | | | 42,324 | Loss |
| D1 | 22/08/1959 | Blackpool | 3-2 | Bolton Wanderers | Hill, Parry R (pen) | | 29,216 | Loss |