| Saturday 21st August 1999 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Bootle | 0-0 | Jarrow Roofing Boldon Community Association | |
| Tuesday 24th August 1999 | F.A. Challenge Cup Preliminary Round Replay | ||
|---|---|---|---|
| Jarrow Roofing Boldon Community Association | 1-1 | Bootle | |
| (After Extra Time, Jarrow Roofing Boldon Community Association won 5-4 on penalties) | |||
| Saturday 25th September 1999 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Crook Town | 5-0 | Bootle | |
