| Premier League | 1 | 1899-09-02 | HOME | Burnley | 2-0 |
| Premier League | 2 | 1899-09-04 | AWAY | Aston Villa | 9-0 |
| Premier League | 3 | 1899-09-09 | AWAY | Preston North End | 1-0 |
| Premier League | 4 | 1899-09-16 | HOME | Nottingham Forest | 3-0 |
| Premier League | 5 | 1899-09-23 | AWAY | Wolverhampton Wanderers | 4-0 |
| Premier League | 6 | 1899-09-30 | AWAY | Stoke City | 1-0 |
| Premier League | 7 | 1899-10-07 | HOME | Sunderland | 0-2 |
| Premier League | 8 | 1899-10-14 | AWAY | West Bromwich Albion | 3-3 |
| Premier League | 8 | 1899-10-21 | HOME | Everton | 1-1 |
| Premier League | 11 | 1899-11-11 | AWAY | Bury | 2-1 |
| Premier League | 11 | 1899-11-18 | HOME | Notts County | 0-0 |
| Premier League | 12 | 1899-11-25 | AWAY | Manchester City | 4-1 |
| Premier League | 13 | 1899-12-02 | HOME | Sheffield United | 2-2 |
| Premier League | 14 | 1899-12-16 | HOME | Aston Villa | 1-0 |
| Premier League | 15 | 1899-12-23 | AWAY | Liverpool | 5-2 |
| Premier League | 17 | 1899-12-26 | AWAY | Derby County | 4-1 |
| Premier League | 17 | 1899-12-30 | AWAY | Burnley | 3-1 |
| Premier League | 18 | 1900-01-06 | HOME | Preston North End | 0-2 |
| Premier League | 19 | 1900-01-13 | AWAY | Nottingham Forest | 5-0 |
| Premier League | 20 | 1900-01-20 | HOME | Wolverhampton Wanderers | 2-3 |
| Premier League | 21 | 1900-02-03 | HOME | Stoke City | 1-2 |
| Premier League | 22 | 1900-02-24 | AWAY | Sunderland | 0-0 |
| Premier League | 21 | 1900-02-27 | HOME | Blackburn Rovers | 4-2 |
| Premier League | 22 | 1900-03-03 | AWAY | Blackburn Rovers | 2-2 |
| Premier League | 25 | 1900-03-14 | AWAY | Newcastle United | 1-0 |
| Premier League | 26 | 1900-03-17 | HOME | Bury | 0-0 |
| Premier League | 27 | 1900-03-24 | AWAY | Notts County | 0-0 |
| Premier League | 28 | 1900-03-31 | HOME | Manchester City | 0-2 |
| Premier League | 29 | 1900-04-07 | AWAY | Sheffield United | 4-0 |
| Premier League | 31 | 1900-04-13 | HOME | Derby County | 1-3 |
| Premier League | 31 | 1900-04-14 | HOME | Newcastle United | 0-0 |
| Premier League | 32 | 1900-04-16 | AWAY | Everton | 4-1 |
| Premier League | 33 | 1900-04-24 | HOME | West Bromwich Albion | 1-1 |
| Premier League | 34 | 1900-04-28 | HOME | Liverpool | 1-2 |
