| D1 | 06/05/1950 | Derby County | 4-0 | Bolton Wanderers | | | 14,622 | Loss |
| D1 | 29/04/1950 | Bolton Wanderers | 2-4 | Wolverhampton Wanderers | Howe (pen), McShane | | 16,345 | Loss |
| D1 | 22/04/1950 | Aston Villa | 3-0 | Bolton Wanderers | | | 29,820 | Loss |
| D1 | 15/04/1950 | Bolton Wanderers | 0-0 | Blackpool | | | 25,800 | Draw |
| D1 | 10/04/1950 | Bolton Wanderers | 1-0 | Chelsea | Hernon | | 24,441 | Win |
| D1 | 08/04/1950 | Middlesbrough | 2-0 | Bolton Wanderers | | | 21,674 | Loss |
| D1 | 07/04/1950 | Chelsea | 1-1 | Bolton Wanderers | McShane | | 52,985 | Draw |
| D1 | 01/04/1950 | Bolton Wanderers | 2-1 | Fulham | Moir, Lofthouse | | 23,658 | Win |
| D1 | 25/03/1950 | Newcastle United | 3-1 | Bolton Wanderers | Moir | | 33,752 | Loss |
| D1 | 18/03/1950 | Bolton Wanderers | 3-0 | Charlton Athletic | Howe (pen), Moir, Langton | | 24,895 | Win |
| D1 | 11/03/1950 | Manchester City | 1-1 | Bolton Wanderers | Lofthouse | | 43,764 | Draw |
| D1 | 08/03/1950 | Bolton Wanderers | 1-2 | Everton | Lofthouse | | 14,807 | Loss |
| D1 | 25/02/1950 | Huddersfield Town | 2-0 | Bolton Wanderers | | | 12,352 | Loss |
| D1 | 18/02/1950 | Bolton Wanderers | 1-0 | Birmingham City | Roberts J (pen) | | 30,383 | Win |
| D1 | 04/02/1950 | Bolton Wanderers | 1-0 | Portsmouth | Lofthouse | | 32,441 | Win |
| FAC4R | 01/02/1950 | Bolton Wanderers | 2-3 | Leeds United | Lofthouse, McShane (aet) | | 29,440 | Loss |
| FAC4 | 28/01/1950 | Leeds United | 1-1 | Bolton Wanderers | Lofthouse | | 51,000 | Draw |
| D1 | 21/01/1950 | Arsenal | 1-1 | Bolton Wanderers | Moir | | 47,493 | Draw |
| D1 | 14/01/1950 | Bolton Wanderers | 3-2 | Liverpool | Howe, Bradley J, McShane | | 41,507 | Win |
| FAC3 | 07/01/1950 | Coventry City | 1-2 | Bolton Wanderers | Lofthouse, Langton | | 29,090 | Win |
| D1 | 31/12/1949 | Sunderland | 2-0 | Bolton Wanderers | | | 38,135 | Loss |
| D1 | 27/12/1949 | West Bromwich Albion | 2-1 | Bolton Wanderers | Bradley J | | 41,746 | Loss |
| D1 | 26/12/1949 | Bolton Wanderers | 3-0 | West Bromwich Albion | Moir 2, Bradley J | | 38,764 | Win |
| D1 | 24/12/1949 | Bolton Wanderers | 0-1 | Burnley | | | 34,461 | Loss |
| D1 | 17/12/1949 | Stoke City | 3-2 | Bolton Wanderers | Moir, Bradley J | | 17,031 | Loss |
| D1 | 10/12/1949 | Wolverhampton Wanderers | 1-1 | Bolton Wanderers | Bradley J | | 30,768 | Draw |
| D1 | 03/12/1949 | Bolton Wanderers | 1-1 | Aston Villa | Barrass | | 22,861 | Draw |
| D1 | 26/11/1949 | Charlton Athletic | 0-0 | Bolton Wanderers | | | 19,755 | Draw |
| D1 | 19/11/1949 | Bolton Wanderers | 3-0 | Manchester City | Roberts J (pen), Lofthouse 2 | | 35,376 | Win |
| D1 | 12/11/1949 | Fulham | 3-0 | Bolton Wanderers | | | 30,197 | Loss |
| D1 | 05/11/1949 | Bolton Wanderers | 2-2 | Newcastle United | Howe, Lofthouse | | 31,728 | Draw |
| D1 | 29/10/1949 | Blackpool | 2-0 | Bolton Wanderers | | | 23,233 | Loss |
| D1 | 22/10/1949 | Bolton Wanderers | 1-2 | Middlesbrough | Murphy D | | 30,095 | Loss |
| D1 | 15/10/1949 | Everton | 0-0 | Bolton Wanderers | | | 38,421 | Draw |
| D1 | 08/10/1949 | Bolton Wanderers | 1-2 | Huddersfield Town | Lofthouse | | 31,048 | Loss |
| D1 | 01/10/1949 | Birmingham City | 0-0 | Bolton Wanderers | | | 33,142 | Draw |
| D1 | 24/09/1949 | Portsmouth | 1-1 | Bolton Wanderers | Lofthouse | | 35,188 | Draw |
| D1 | 17/09/1949 | Bolton Wanderers | 2-2 | Arsenal | Roberts J (pen), Barrass | | 33,867 | Draw |
| D1 | 10/09/1949 | Liverpool | 1-1 | Bolton Wanderers | Bradley J | | 44,212 | Draw |
| D1 | 05/09/1949 | Bolton Wanderers | 0-0 | Derby County | | | 29,558 | Draw |
| D1 | 03/09/1949 | Bolton Wanderers | 2-1 | Sunderland | Howe (pen), Moir | | 32,092 | Win |
| D1 | 31/08/1949 | Bolton Wanderers | 1-2 | Manchester United | McShane | | 39,226 | Loss |
| D1 | 27/08/1949 | Burnley | 2-1 | Bolton Wanderers | Woodward | | 31,581 | Loss |
| D1 | 24/08/1949 | Manchester United | 3-0 | Bolton Wanderers | | | 42,515 | Loss |
| D1 | 20/08/1949 | Bolton Wanderers | 4-0 | Stoke City | Bradley J 2, Lofthouse, Moir | | 32,222 | Win |