| Saturday 21st August 1999 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Newcastle Town | 1-0 | Sandwell Borough | |
| Saturday 4th September 1999 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Wellingborough Town | 2-2 | Newcastle Town | |
| Tuesday 7th September 1999 | F.A. Challenge Cup 1st Qualifying Round Replay | ||
|---|---|---|---|
| Newcastle Town | 0-4 | Wellingborough Town | |
| Saturday 25th September 1999 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Newcastle Town | 4-0 | Dudley Town | |
| Saturday 23rd October 1999 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| Long Eaton United | 0-5 | Newcastle Town | |
| Saturday 13th November 1999 | F.A. Carlsberg Vase 2nd Round | ||
|---|---|---|---|
| Newcastle Town | 2-1 | Desborough Town | |
| Saturday 4th December 1999 | F.A. Carlsberg Vase 3rd Round | ||
|---|---|---|---|
| Newcastle Town | 2-1 | Clitheroe | |
| Saturday 22nd January 2000 | F.A. Carlsberg Vase 4th Round | ||
|---|---|---|---|
| Letchworth | 0-2 | Newcastle Town | |
| Saturday 12th February 2000 | F.A. Carlsberg Vase 5th Round | ||
|---|---|---|---|
| Chasetown | 0-0 | Newcastle Town | |
| (After Extra Time, 0-0 after 90 mins) | |||
| Newcastle Town | 0-0 | Chasetown | |
| (After Extra Time, Newcastle Town won 4-3 on penalties) | |||
| Saturday 26th February 2000 | F.A. Carlsberg Vase Quarter Finals | ||
|---|---|---|---|
| Ramsgate | 0-1 | Newcastle Town | |
| Saturday 18th March 2000 | F.A. Carlsberg Vase Semi Finals | ||
|---|---|---|---|
| Newcastle Town | 0-2 | Deal Town | |
| Saturday 25th March 2000 | F.A. Carlsberg Vase Semi Finals | ||
|---|---|---|---|
| Deal Town | 1-1 | Newcastle Town | |
