| Bury FC v Wolverhampton Wanderers FC 02/09/1899 | View match | |
| Morton FC v Hamilton Academicals 02/09/1899 | View match | |
| Ayr FC v Linthouse 02/09/1899 | View match | |
| Dundee v Clyde 02/09/1899 | View match | |
| St Mirren FC v St Bernard`s 02/09/1899 | View match | |
| The Wednesday v Chesterfield Town 02/09/1899 | View match | |
| Woolwich Arsenal v Leicester Fosse 02/09/1899 | View match | |
| Birmingham v Walsall FC 02/09/1899 | View match | |
| Aston Villa FC v Glossop North End 04/09/1899 | View match | |
| Burslem Port Vale v Middlesbrough FC 04/09/1899 | View match | |
| Burslem Port Vale v Grimsby Town FC 09/09/1899 | View match | |
| Burton Swifts v Loughborough United 09/09/1899 | View match |