| D1 | 06/05/1939 | Chelsea | 1-1 | Bolton Wanderers | Howe | | 18,232 | Draw |
| D1 | 29/04/1939 | Bolton Wanderers | 0-0 | Manchester United | | | 10,314 | Draw |
| D1 | 26/04/1939 | Bolton Wanderers | 0-2 | Preston North End | | | 15,353 | Loss |
| D1 | 22/04/1939 | Bolton Wanderers | 0-0 | Wolverhampton Wanderers | | | 23,796 | Draw |
| D1 | 15/04/1939 | Aston Villa | 1-3 | Bolton Wanderers | Currier, Sinclair, Cobley (og) | | 23,160 | Win |
| D1 | 10/04/1939 | Stoke City | 4-1 | Bolton Wanderers | Hunt G | | 29,042 | Loss |
| D1 | 08/04/1939 | Bolton Wanderers | 2-1 | Sunderland | Hunt G, Westwood | | 22,692 | Win |
| D1 | 01/04/1939 | Grimsby Town | 1-1 | Bolton Wanderers | Hunt G | | 8,558 | Draw |
| D1 | 25/03/1939 | Bolton Wanderers | 2-1 | Derby County | Hunt G, Westwood | | 20,543 | Win |
| D1 | 18/03/1939 | Blackpool | 0-0 | Bolton Wanderers | | | 18,896 | Draw |
| D1 | 11/03/1939 | Bolton Wanderers | 1-1 | Brentford | Hunt G | | 15,161 | Draw |
| D1 | 04/03/1939 | Arsenal | 3-1 | Bolton Wanderers | Hunt G | | 29,814 | Loss |
| D1 | 25/02/1939 | Bolton Wanderers | 3-2 | Huddersfield Town | Hunt G 2, Howe | | 19,322 | Win |
| D1 | 22/02/1939 | Bolton Wanderers | 3-0 | Birmingham City | Hunt G 2, Howe | | 11,696 | Win |
| D1 | 18/02/1939 | Everton | 2-1 | Bolton Wanderers | Geldard | | 38,961 | Loss |
| D1 | 04/02/1939 | Middlesbrough | 1-2 | Bolton Wanderers | Sinclair 2 | | 16,416 | Win |
| D1 | 28/01/1939 | Bolton Wanderers | 4-0 | Leicester City | Sinclair, Howe 2, Hunt G | | 18,621 | Win |
| D1 | 21/01/1939 | Liverpool | 1-2 | Bolton Wanderers | Hunt G, Sinclair | | 17,703 | Win |
| FAC3R2 | 16/01/1939 | Bolton Wanderers | 0-1 | Middlesbrough | (played at Elland Road, Leeds) | | 25,577 | Loss |
| D1 | 14/01/1939 | Bolton Wanderers | 2-2 | Leeds United | Goslin 2 (1 pen) | | 14,893 | Draw |
| FAC3R | 11/01/1939 | Bolton Wanderers | 0-0 | Middlesbrough | (aet) | | 16,981 | Draw |
| FAC3 | 07/01/1939 | Middlesbrough | 0-0 | Bolton Wanderers | | | 32,790 | Draw |
| D1 | 02/01/1939 | Bolton Wanderers | 1-3 | Stoke City | Currier | | 24,762 | Loss |
| D1 | 31/12/1938 | Bolton Wanderers | 5-1 | Portsmouth | Goslin (pen), Hunt G 2, Grosvenor, Roberts J | | 15,679 | Win |
| D1 | 27/12/1938 | Preston North End | 2-2 | Bolton Wanderers | Howe, Roberts J | | 38,240 | Draw |
| D1 | 24/12/1938 | Charlton Athletic | 2-1 | Bolton Wanderers | Howe | | 6,590 | Loss |
| D1 | 17/12/1938 | Wolverhampton Wanderers | 1-1 | Bolton Wanderers | Howe | | 19,316 | Draw |
| D1 | 10/12/1938 | Bolton Wanderers | 1-2 | Aston Villa | Currier | | 22,552 | Loss |
| D1 | 03/12/1938 | Sunderland | 2-2 | Bolton Wanderers | Hunt G, Howe | | 17,815 | Draw |
| D1 | 26/11/1938 | Bolton Wanderers | 1-1 | Grimsby Town | Currier | | 16,229 | Draw |
| D1 | 19/11/1938 | Derby County | 3-0 | Bolton Wanderers | | | 26,062 | Loss |
| D1 | 12/11/1938 | Bolton Wanderers | 0-1 | Blackpool | | | 35,782 | Loss |
| D1 | 05/11/1938 | Brentford | 2-2 | Bolton Wanderers | Westwood, Hunt G | | 24,594 | Draw |
| D1 | 29/10/1938 | Bolton Wanderers | 1-1 | Arsenal | Woodward | | 46,611 | Draw |
| D1 | 22/10/1938 | Huddersfield Town | 2-1 | Bolton Wanderers | Roberts J | | 18,027 | Loss |
| D1 | 15/10/1938 | Bolton Wanderers | 4-2 | Everton | Roberts J 3, Woodward | | 54,564 | Win |
| D1 | 08/10/1938 | Birmingham City | 0-2 | Bolton Wanderers | Westwood, Hunt G | | 21,855 | Win |
| D1 | 01/10/1938 | Bolton Wanderers | 4-1 | Middlesbrough | Westwood 2, Rothwell, Roberts J | | 28,505 | Win |
| D1 | 24/09/1938 | Leicester City | 0-0 | Bolton Wanderers | | | 18,263 | Draw |
| D1 | 17/09/1938 | Bolton Wanderers | 3-1 | Liverpool | Hunt G 2, Roberts J | | 22,409 | Win |
| D1 | 10/09/1938 | Leeds United | 1-2 | Bolton Wanderers | Hunt G, Woodward | | 20,381 | Win |
| D1 | 05/09/1938 | Bolton Wanderers | 0-2 | Chelsea | | | 19,616 | Loss |
| D1 | 03/09/1938 | Portsmouth | 2-1 | Bolton Wanderers | Grosvenor | | 28,452 | Loss |
| D1 | 31/08/1938 | Manchester United | 2-2 | Bolton Wanderers | Hunt G 2 | | 37,950 | Draw |
| D1 | 27/08/1938 | Bolton Wanderers | 2-1 | Charlton Athletic | Hunt G, Anderson | | 21,809 | Win |