| Leicester Fosse v Burton Swifts 16/09/1899 | View match | |
| Barnsley FC v Luton Town FC 16/09/1899 | View match | |
| Birmingham v Chesterfield FC 16/09/1899 | View match | |
| Morton FC v Ayr FC 16/09/1899 | View match | |
| Abercorn v Port Glasgow Athletic 16/09/1899 | View match | |
| Kilmarnock FC v St Bernard`s 16/09/1899 | View match | |
| Dundee v Hibernian FC 16/09/1899 | View match | |
| Heart Of Midlothian (Hearts) v St Mirren FC 16/09/1899 | View match | |
| Leith Athletic v Airdrieonians (Old) 16/09/1899 | View match | |
| The Wednesday v Bolton Wanderers FC 16/09/1899 | View match | |
| Bury FC v Manchester City FC 16/09/1899 | View match | |
| Small Heath v Chesterfield Town 16/09/1899 | View match |