| Saturday 11th September 1999 | F.A. Carlsberg Vase 1st Qualifying Round | ||
|---|---|---|---|
| Squires Gate | 2-1 | Sheffield | |
| Saturday 25th September 1999 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Yorkshire Amateur | 1-1 | Squires Gate | |
| (After Extra Time, 1-1 after 90 mins) | |||
| Tuesday 28th September 1999 | F.A. Carlsberg Vase | ||
|---|---|---|---|
| Squires Gate | 2-1 | Yorkshire Amateur | |
| Saturday 23rd October 1999 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| Squires Gate | 3-3 | Ramsbottom United | |
| (After Extra Time, 2-2 after 90 mins) | |||
| Tuesday 26th October 1999 | F.A. Carlsberg Vase | ||
|---|---|---|---|
| Ramsbottom United | 5-3 | Squires Gate | |
| (After Extra Time, 3-3 after 90 mins) | |||
