| Comp | Date | Home | Score | Away | Scorers | Video | Attendance | Result |
|---|---|---|---|---|---|---|---|---|
| D1 | 29/04/1899 | Preston North End | 0-1 | Bolton Wanderers | Morgan H | Unknown | Win | |
| D1 | 17/04/1899 | Bolton Wanderers | 0-0 | Aston Villa | Unknown | Draw | ||
| D1 | 15/04/1899 | Bury | 3-1 | Bolton Wanderers | McAteer T | Unknown | Loss | |
| D1 | 08/04/1899 | Nottingham Forest | 1-2 | Bolton Wanderers | Morgan H 2 | Unknown | Win | |
| D1 | 04/04/1899 | Wolverhampton Wanderers | 1-0 | Bolton Wanderers | Unknown | Loss | ||
| D1 | 03/04/1899 | Notts County | 2-1 | Bolton Wanderers | McAteer T | Unknown | Loss | |
| D1 | 01/04/1899 | Bolton Wanderers | 2-1 | Liverpool | McAteer T, Morgan H | Unknown | Win | |
| D1 | 31/03/1899 | Bolton Wanderers | 2-1 | Derby County | Morgan H, Barlow | Unknown | Win | |
| D1 | 18/03/1899 | Bolton Wanderers | 0-0 | Newcastle United | Unknown | Draw | ||
| D1 | 11/03/1899 | Sheffield United | 3-1 | Bolton Wanderers | Morgan H | Unknown | Loss | |
| D1 | 25/02/1899 | Bolton Wanderers | 2-4 | Everton | Barlow 2 | Unknown | Loss | |
| D1 | 18/02/1899 | Bolton Wanderers | 0-2 | Stoke City | Unknown | Loss | ||
| FAC1R | 01/02/1899 | Bolton Wanderers | 0-1 | Wolverhampton Wanderers | Unknown | Loss | ||
| FAC1 | 28/01/1899 | Wolverhampton Wanderers | 0-0 | Bolton Wanderers | Unknown | Draw | ||
| D1 | 21/01/1899 | Bolton Wanderers | 6-1 | Sunderland | Gilligan A 2, Brown R 2, Barlow, Barnes J | Unknown | Win | |
| D1 | 14/01/1899 | Sheffield Wednesday | 1-0 | Bolton Wanderers | Unknown | Loss | ||
| D1 | 07/01/1899 | Bolton Wanderers | 0-2 | Blackburn Rovers | Unknown | Loss | ||
| D1 | 03/01/1899 | Bolton Wanderers | 2-0 | Burnley | Brown R, Jack R | Unknown | Win | |
| D1 | 31/12/1898 | West Bromwich Albion | 1-0 | Bolton Wanderers | Unknown | Loss | ||
| D1 | 26/12/1898 | Derby County | 1-1 | Bolton Wanderers | Barlow | Unknown | Draw | |
| D1 | 17/12/1898 | Bolton Wanderers | 0-1 | Bury | Unknown | Loss | ||
| D1 | 10/12/1898 | Bolton Wanderers | 0-2 | Nottingham Forest | Unknown | Loss | ||
| D1 | 03/12/1898 | Liverpool | 2-0 | Bolton Wanderers | Unknown | Loss | ||
| D1 | 26/11/1898 | Bolton Wanderers | 2-2 | Preston North End | Gilligan A, Miller T | Unknown | Draw | |
| D1 | 19/11/1898 | Newcastle United | 4-1 | Bolton Wanderers | Miller T | Unknown | Loss | |
| D1 | 12/11/1898 | Bolton Wanderers | 3-0 | Sheffield United | Gilligan A 2, Jack R | Unknown | Win | |
| D1 | 05/11/1898 | Burnley | 2-0 | Bolton Wanderers | Unknown | Loss | ||
| D1 | 29/10/1898 | Aston Villa | 2-1 | Bolton Wanderers | Gilligan A | Unknown | Loss | |
| D1 | 22/10/1898 | Stoke City | 2-3 | Bolton Wanderers | Miller T, Freebairn, Nicoll | Unknown | Win | |
| D1 | 15/10/1898 | Bolton Wanderers | 0-1 | Notts County | Unknown | Loss | ||
| D1 | 08/10/1898 | Everton | 1-0 | Bolton Wanderers | Unknown | Loss | ||
| D1 | 01/10/1898 | Bolton Wanderers | 2-1 | Wolverhampton Wanderers | Wright J 2 | Unknown | Win | |
| D1 | 24/09/1898 | Sunderland | 0-0 | Bolton Wanderers | Unknown | Draw | ||
| D1 | 17/09/1898 | Bolton Wanderers | 0-0 | Sheffield Wednesday | Unknown | Draw | ||
| D1 | 10/09/1898 | Blackburn Rovers | 4-1 | Bolton Wanderers | Miller T | Unknown | Loss | |
| D1 | 03/09/1898 | Bolton Wanderers | 3-3 | West Bromwich Albion | Nicoll, Wright J, Miller T | Unknown | Draw |