| Continental Star Sunday FC | 2 | 1 | Sheldon Heath Social OB |
After extra time (1-1 at full time)
Sunday 25th February, 2001
Sunday 24th December, 2000
| Farthings Athletic FC | 2 | 3 | Continental Star Sunday FC |
| Maudslay FC | 0 | 1 | Triplex Star FC |
| Baldwin & Williams FC | 2 | 3 | Sheldon Heath Social OB |
| Olton Royal OB FC | 0 | 1 | Beeches Old Boys FC |
Round 2
Sunday 26th November, 2000
| Beeches Old Boys FC | 4 | 2 | Flickers 83 FC |
| Olton Royal OB FC | 4 | 2 | Wychall Wanderers FC* |
| Maudslay FC | 7 | 2 | Hamstead & Great Barr FC |
| Farthings Athletic FC | 7 | 2 | Longbridge Sports & Social FC |
| Bartley Green Veterans FC | 1 | 2 | Sheldon Heath Social OB FC |
| Moor Lane Old Boys FC | 0 | 1 | Baldwin & Williams FC |
| Brookvale Social Old Boys FC | 1 | 2 | Continental Star Sunday FC |
| Thorn FC | 1 | 2 | Triplex Star FC |
Sun 22nd October, 2000
| Beeches Old Boys | 4 | 2 | Beaufort Lloyds/TSB OB FC |
| O'Neills Veterans FC | 0 | 2 | Longbridge Sports & Social FC |
| Windermere Sporting FC | 2 | 3 | Continental Star Sunday FC* |
| Ward End Ex Service FC | 3 | 6 | Farthings Athletic FC |
| Hamstead & Great Barr FC | 4 | 2 | St Gerards Old Boys FC |
| Bromford Bridge FC | 0 | 6 | Brookvale Social Old Boys FC |
| Triplex Star FC | 2 | 1 | Brooklands/Jaguar FC |
| # Baldwin & Williams FC | 4 | 1 | Folly Lane BCOB Assoc Sun FC |
| Maudslay FC | 4 | 0 | Weddington Wanderers FC |
| Wychall Wanderers FC | 3 | 0 | Case Star FC |
| Sheldon Heath Social Old Boys | 5 | 1 | St Philips Veterans FC |
| Smithswood S & S O35's FC | 0 | 4 | Olton Royale OB FC |
| Concorde FC | 1 | 5 | Flickers 83 FC |
| Bartley Green Veterans FC | 4 | 1 | Oscott Liberals Old Boys FC |
| Hundred Acre FC | 2 | 3 | Moor Lane Old Boys FC |
| Chelmsley Wood Cons 94 FC | 0 | 3 | Thorn FC |