| D2 | 28/04/1900 | Bolton Wanderers | 5-0 | Burton Swifts | Bell L 4, Morgan H | | Unknown | Win |
| D2 | 23/04/1900 | Port Vale | 0-2 | Bolton Wanderers | Bell L 2 | | Unknown | Win |
| D2 | 21/04/1900 | Bolton Wanderers | 3-0 | Gainsborough Trinity | Chorlton 2, Bell L | | 4,327 | Win |
| D2 | 16/04/1900 | Brighton | 3-1 | Bolton Wanderers | Picken J | | Unknown | Loss |
| D2 | 14/04/1900 | Bolton Wanderers | 3-0 | Chesterfield | Picken J, Gilligan A, Morgan H | | Unknown | Win |
| D2 | 13/04/1900 | Bolton Wanderers | 2-0 | Barnsley | Bell L, Morgan H | | Unknown | Win |
| D2 | 07/04/1900 | Middlesbrough | 0-3 | Bolton Wanderers | Morgan H, Hanson J, Bell L | | Unknown | Win |
| D2 | 31/03/1900 | Bolton Wanderers | 2-0 | Walsall | Brown R, Bell L | | Unknown | Win |
| D2 | 17/03/1900 | Bolton Wanderers | 3-0 | Luton Town | Jack R, Morgan H, Opponent (og) | | 3,658 | Win |
| D2 | 10/03/1900 | Leicester Fosse | 0-0 | Bolton Wanderers | | | Unknown | Draw |
| D2 | 24/02/1900 | Woolwich Arsenal | 0-1 | Bolton Wanderers | Bell L | | Unknown | Win |
| D2 | 17/02/1900 | Bolton Wanderers | 1-2 | Grimsby Town | Gilligan A | | Unknown | Loss |
| D2 | 03/02/1900 | Bolton Wanderers | 1-1 | Small Heath | Fitchett | | Unknown | Draw |
| FAC1 | 27/01/1900 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | | 12,390 | Loss |
| D2 | 20/01/1900 | Lincoln City | 1-0 | Bolton Wanderers | | | Unknown | Loss |
| D2 | 13/01/1900 | Bolton Wanderers | 1-0 | Sheffield Wednesday | Jack R | | 12,325 | Win |
| D2 | 06/01/1900 | Newton Heath | 1-2 | Bolton Wanderers | Picken J, Morgan H | | Unknown | Win |
| D2 | 02/01/1900 | Bolton Wanderers | 5-0 | Port Vale | McAteer T 3, Jack R 2 | | Unknown | Win |
| D2 | 01/01/1900 | Bolton Wanderers | 2-1 | Brighton | Bell L 2 | | Unknown | Win |
| D2 | 30/12/1899 | Bolton Wanderers | 7-0 | Loughborough | Hanson J 2, Morgan H, Bell L 3, McAteer T | | Unknown | Win |
| D2 | 26/12/1899 | Barnsley | 1-6 | Bolton Wanderers | Picken J, Freebairn, Hanson J 3, Morgan H | | Unknown | Win |
| D2 | 23/12/1899 | Burton Swifts | 2-5 | Bolton Wanderers | Bell L 2, Morgan H, Picken J, Freebairn | | Unknown | Win |
| D2 | 16/12/1899 | Gainsborough Trinity | 1-1 | Bolton Wanderers | Barlow | | Unknown | Draw |
| D2 | 06/12/1899 | Chesterfield | 3-3 | Bolton Wanderers | Jack R, Barlow, Picken J | | Unknown | Draw |
| D2 | 02/12/1899 | Bolton Wanderers | 3-0 | Middlesbrough | Brown R, Jack R, Fitchett | | Unknown | Win |
| D2 | 25/11/1899 | Walsall | 2-2 | Bolton Wanderers | Barlow, Picken J | | Unknown | Draw |
| D2 | 11/11/1899 | Luton Town | 0-2 | Bolton Wanderers | Barlow 2 | | Unknown | Win |
| D2 | 04/11/1899 | Bolton Wanderers | 2-2 | Leicester Fosse | Bell L, Morgan H | | Unknown | Draw |
| D2 | 21/10/1899 | Bolton Wanderers | 1-0 | Woolwich Arsenal | Barlow | | Unknown | Win |
| D2 | 14/10/1899 | Grimsby Town | 0-0 | Bolton Wanderers | | | Unknown | Draw |
| D2 | 30/09/1899 | Small Heath | 0-0 | Bolton Wanderers | | | Unknown | Draw |
| D2 | 23/09/1899 | Bolton Wanderers | 4-0 | Lincoln City | Gilligan A, Bell L, Fitchett, Somerville | | Unknown | Win |
| D2 | 16/09/1899 | Sheffield Wednesday | 2-1 | Bolton Wanderers | Opponent (og) | | Unknown | Loss |
| D2 | 09/09/1899 | Bolton Wanderers | 2-1 | Newton Heath | Bell L 2 | | Unknown | Win |
| D2 | 02/09/1899 | Loughborough | 2-3 | Bolton Wanderers | Bell L, McAteer T, Jack R | | Unknown | Win |