| D1 | 25/04/1959 | Bolton Wanderers | 3-1 | Blackburn Rovers | Lofthouse, Parry R 2 (1 pen) | | 18,268 | Win |
| D1 | 22/04/1959 | Newcastle United | 2-0 | Bolton Wanderers | | | 17,451 | Loss |
| D1 | 18/04/1959 | Portsmouth | 0-1 | Bolton Wanderers | Lofthouse | | 14,161 | Win |
| D1 | 14/04/1959 | Burnley | 0-1 | Bolton Wanderers | Lofthouse | | 23,664 | Win |
| D1 | 11/04/1959 | Bolton Wanderers | 2-2 | Wolverhampton Wanderers | Lofthouse, Parry R (pen) | | 26,019 | Draw |
| D1 | 08/04/1959 | Birmingham City | 1-3 | Bolton Wanderers | Birch, Riley, Lofthouse | | 24,608 | Win |
| D1 | 04/04/1959 | Manchester United | 3-0 | Bolton Wanderers | | | 61,528 | Loss |
| D1 | 30/03/1959 | Leicester City | 0-0 | Bolton Wanderers | | | 20,329 | Draw |
| D1 | 28/03/1959 | Bolton Wanderers | 4-1 | Tottenham Hotspur | Parry R 2, Stevens D, Baker (og) | | 21,384 | Win |
| D1 | 27/03/1959 | Bolton Wanderers | 3-3 | Leicester City | Ogilvie (og)*, Stevens D, Lofthouse (own goal by Chalmers) | | 21,212 | Draw |
| D1 | 21/03/1959 | West Ham United | 4-3 | Bolton Wanderers | Stevens D, Parry R, Hill | | 27,722 | Loss |
| D1 | 18/03/1959 | Bolton Wanderers | 1-3 | Aston Villa | Lofthouse | | 21,808 | Loss |
| D1 | 07/03/1959 | Blackpool | 4-0 | Bolton Wanderers | | | 21,072 | Loss |
| D1 | 04/03/1959 | Bolton Wanderers | 6-0 | Chelsea | Lofthouse 2, Parry R, Hill 3 (1 pen) | | 24,258 | Win |
| FACQF | 28/02/1959 | Nottingham Forest | 2-1 | Bolton Wanderers | Birch | | 45,000 | Loss |
| FAC5R2 | 23/02/1959 | Bolton Wanderers | 1-0 | Preston North End | Lofthouse (played at Ewood Park, Blackburn) | | 51,090 | Win |
| D1 | 21/02/1959 | Bolton Wanderers | 2-1 | Preston North End | Birch, Hill | | 16,472 | Win |
| FAC5R | 18/02/1959 | Preston North End | 1-1 | Bolton Wanderers | Holden D (aet) | | 36,866 | Draw |
| FAC5 | 14/02/1959 | Bolton Wanderers | 2-2 | Preston North End | Birch, Parry R | | 58,692 | Draw |
| D1 | 07/02/1959 | Nottingham Forest | 3-0 | Bolton Wanderers | | | 29,703 | Loss |
| D1 | 31/01/1959 | Bolton Wanderers | 4-2 | Luton Town | Lofthouse 3 (1 pen), Holden D | | 27,787 | Win |
| FAC4 | 24/01/1959 | Wolverhampton Wanderers | 1-2 | Bolton Wanderers | Lofthouse, Parry R (pen) | | 55,621 | Win |
| FAC3 | 10/01/1959 | Scunthorpe United | 0-2 | Bolton Wanderers | Lofthouse 2 | | 23,708 | Win |
| D1 | 03/01/1959 | Bolton Wanderers | 2-1 | West Bromwich Albion | Lofthouse 2 | | 27,847 | Win |
| D1 | 27/12/1958 | Bolton Wanderers | 0-3 | Everton | | | 37,263 | Loss |
| D1 | 26/12/1958 | Everton | 1-0 | Bolton Wanderers | | | 61,692 | Loss |
| D1 | 20/12/1958 | Leeds United | 3-4 | Bolton Wanderers | Edwards G B, Lofthouse 2, Gibson (og) | | 28,534 | Win |
| D1 | 13/12/1958 | Bolton Wanderers | 1-1 | Newcastle United | Stevens D | | 23,020 | Draw |
| D1 | 06/12/1958 | Blackburn Rovers | 1-1 | Bolton Wanderers | Stevens D | | 38,027 | Draw |
| D1 | 29/11/1958 | Bolton Wanderers | 2-1 | Portsmouth | Stevens D, Lofthouse | | 20,624 | Win |
| D1 | 22/11/1958 | Wolverhampton Wanderers | 1-2 | Bolton Wanderers | Stevens D, Lofthouse | | 33,489 | Win |
| D1 | 15/11/1958 | Bolton Wanderers | 6-3 | Manchester United | Edwards G B, Stevens D 2, Parry R (pen), Gubbins 2 | | 33,358 | Win |
| D1 | 08/11/1958 | Tottenham Hotspur | 1-1 | Bolton Wanderers | Lofthouse | | 39,820 | Draw |
| D1 | 01/11/1958 | Bolton Wanderers | 0-2 | West Ham United | | | 31,067 | Loss |
| D1 | 25/10/1958 | Aston Villa | 2-1 | Bolton Wanderers | Stevens D | | 28,740 | Loss |
| D1 | 18/10/1958 | Bolton Wanderers | 4-0 | Blackpool | Stevens D, Holden D, Hill 2 (1 pen) | | 37,045 | Win |
| D1 | 11/10/1958 | Chelsea | 0-1 | Bolton Wanderers | Lofthouse | | 49,229 | Win |
| CS | 06/10/1958 | Bolton Wanderers | 4-1 | Wolverhampton Wanderers | Lofthouse 2, Bannister N, Hill (pen) | | 15,239 | Win |
| D1 | 04/10/1958 | Preston North End | 0-0 | Bolton Wanderers | | | 28,769 | Draw |
| D1 | 27/09/1958 | Bolton Wanderers | 1-2 | Burnley | Lofthouse | | 32,359 | Loss |
| D1 | 20/09/1958 | Bolton Wanderers | 3-2 | Nottingham Forest | Stevens D, Lofthouse 2 | | 28,486 | Win |
| D1 | 17/09/1958 | Bolton Wanderers | 2-1 | Arsenal | Birch, Lofthouse | | 42,200 | Win |
| D1 | 13/09/1958 | Luton Town | 0-0 | Bolton Wanderers | | | 19,699 | Draw |
| D1 | 09/09/1958 | Arsenal | 6-1 | Bolton Wanderers | Parry R (pen) | | 45,276 | Loss |
| D1 | 06/09/1958 | Bolton Wanderers | 2-0 | Birmingham City | Edwards G B, Lofthouse | | 24,707 | Win |
| D1 | 03/09/1958 | Bolton Wanderers | 4-1 | Manchester City | Birch, Stevens D, Lofthouse, Parry R | | 39,727 | Win |
| D1 | 30/08/1958 | West Bromwich Albion | 1-1 | Bolton Wanderers | Edwards G B | | 37,244 | Draw |
| D1 | 27/08/1958 | Manchester City | 3-3 | Bolton Wanderers | Birch, Parry R (pen), Lofthouse | | 40,844 | Draw |
| D1 | 23/08/1958 | Bolton Wanderers | 4-0 | Leeds United | Birch, Parry R, Lofthouse 2 | | 25,922 | Win |