| Morton FC v Leith Athletic 30/09/1899 | View match | |
| St Mirren FC v Clyde 30/09/1899 | View match | |
| Kilmarnock FC v Third Lanark 30/09/1899 | View match | |
| The Wednesday v Newton Heath 30/09/1899 | View match | |
| Small Heath v Lincoln City FC 02/10/1899 | View match | |
| Birmingham v Lincoln City FC 02/10/1899 | View match | |
| Notts County FC v Liverpool FC 05/10/1899 | View match | |
| Preston North End FC v Everton FC 07/10/1899 | View match | |
| Liverpool FC v Derby County FC 07/10/1899 | View match | |
| Nottingham Forest FC v West Bromwich Albion FC 07/10/1899 | View match | |
| Burnley FC v Blackburn Rovers FC 07/10/1899 | View match | |
| Wolverhampton Wanderers FC v Stoke 07/10/1899 | View match |