| D2 | 30/04/1909 | Bolton Wanderers | 1-0 | Derby County | Hughes W | | Unknown | Win |
| D2 | 24/04/1909 | Clapton Orient | 0-2 | Bolton Wanderers | Hughes W 2 | | Unknown | Win |
| D2 | 17/04/1909 | Bolton Wanderers | 4-1 | Stockport County | Hughes W 2, Hunter 2 | | Unknown | Win |
| D2 | 12/04/1909 | West Bromwich Albion | 2-0 | Bolton Wanderers | | | Unknown | Loss |
| D2 | 10/04/1909 | Oldham Athletic | 1-1 | Bolton Wanderers | Hogan | | Unknown | Draw |
| D2 | 03/04/1909 | Bolton Wanderers | 2-0 | Glossop North End | Owen J 2 | | Unknown | Win |
| D2 | 27/03/1909 | Wolverhampton Wanderers | 1-2 | Bolton Wanderers | Hogan, Hughes W | | Unknown | Win |
| D2 | 13/03/1909 | Bradford | 1-2 | Bolton Wanderers | Greenhalgh S, Hogan | | Unknown | Win |
| D2 | 06/03/1909 | Bolton Wanderers | 3-1 | Blackpool | Owen J 2, Hunter | | Unknown | Win |
| D2 | 27/02/1909 | Burnley | 1-2 | Bolton Wanderers | Hughes W, Hunter | | Unknown | Win |
| D2 | 20/02/1909 | Bolton Wanderers | 4-0 | Chesterfield | Hunter, Barber, Owen J, Hughes W | | Unknown | Win |
| D2 | 13/02/1909 | Fulham | 1-2 | Bolton Wanderers | Hughes W, Hogan | | Unknown | Win |
| D2 | 30/01/1909 | Grimsby Town | 1-0 | Bolton Wanderers | | | Unknown | Loss |
| D2 | 23/01/1909 | Bolton Wanderers | 0-1 | Tottenham Hotspur | | | Unknown | Loss |
| FAC1 | 16/01/1909 | West Bromwich Albion | 3-1 | Bolton Wanderers | Hunter | | Unknown | Loss |
| D2 | 09/01/1909 | Gainsborough Trinity | 2-1 | Bolton Wanderers | Greenhalgh S | | Unknown | Loss |
| D2 | 02/01/1909 | Bolton Wanderers | 3-0 | Barnsley | Owen J 2, Hughes W | | Unknown | Win |
| D2 | 01/01/1909 | Bolton Wanderers | 2-1 | Birmingham City | Hughes W, Hogan | | Unknown | Win |
| D2 | 26/12/1908 | Leeds City | 1-2 | Bolton Wanderers | Hughes W, Stokes | | Unknown | Win |
| D2 | 25/12/1908 | Bolton Wanderers | 2-0 | Leeds City | Hogan, Hughes W | | Unknown | Win |
| D2 | 19/12/1908 | Bolton Wanderers | 2-0 | Clapton Orient | Hughes W 2 | | Unknown | Win |
| D2 | 12/12/1908 | Stockport County | 1-0 | Bolton Wanderers | | | Unknown | Loss |
| D2 | 03/12/1908 | Bolton Wanderers | 3-0 | Oldham Athletic | Greenhalgh S, Hughes W, Hogan | | Unknown | Win |
| D2 | 28/11/1908 | Glossop North End | 0-2 | Bolton Wanderers | Hogan 2 | | Unknown | Win |
| D2 | 21/11/1908 | Bolton Wanderers | 1-1 | Wolverhampton Wanderers | Shepherd | | Unknown | Draw |
| D2 | 14/11/1908 | Chesterfield | 0-2 | Bolton Wanderers | Hogan 2 | | Unknown | Win |
| D2 | 07/11/1908 | Bolton Wanderers | 0-1 | Bradford | | | Unknown | Loss |
| D2 | 31/10/1908 | Blackpool | 1-2 | Bolton Wanderers | Shepherd, Barber | | Unknown | Win |
| D2 | 24/10/1908 | Bolton Wanderers | 2-1 | Burnley | Woods S, McEwan | | Unknown | Win |
| D2 | 17/10/1908 | Derby County | 1-0 | Bolton Wanderers | | | Unknown | Loss |
| D2 | 10/10/1908 | Bolton Wanderers | 0-0 | Fulham | | | Unknown | Draw |
| D2 | 03/10/1908 | Hull City | 2-0 | Bolton Wanderers | | | Unknown | Loss |
| D2 | 26/09/1908 | Bolton Wanderers | 2-0 | Grimsby Town | Shepherd, McClarence | | Unknown | Win |
| D2 | 19/09/1908 | Tottenham Hotspur | 2-1 | Bolton Wanderers | Woods S | | Unknown | Loss |
| D2 | 15/09/1908 | Bolton Wanderers | 1-1 | West Bromwich Albion | Owen J | | Unknown | Draw |
| D2 | 14/09/1908 | Bolton Wanderers | 1-0 | Hull City | Stuart | | Unknown | Win |
| D2 | 12/09/1908 | Bolton Wanderers | 4-0 | Gainsborough Trinity | Baverstock H, McClarence 2, White | | Unknown | Win |
| D2 | 05/09/1908 | Barnsley | 0-1 | Bolton Wanderers | McClarence | | Unknown | Win |
| D2 | 02/09/1908 | Birmingham City | 2-0 | Bolton Wanderers | | | Unknown | Loss |