| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 02.11.1999 | 1. Round | 1. Round | A | ![]() | Merthyr Tydfil FC | D | 2:22:0 |
| 09.11.1999 | 1. Round Repeat | 1. Round Repeat | H | ![]() | Merthyr Tydfil FC | W | 3:12:1 |
| 20.11.1999 | 2. Round | 2. Rd | H | ![]() | Chester City | L | 1:21:1 |
Stalybridge Celtic


| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 02.11.1999 | 1. Round | 1. Round | A | ![]() | Merthyr Tydfil FC | D | 2:22:0 |
| 09.11.1999 | 1. Round Repeat | 1. Round Repeat | H | ![]() | Merthyr Tydfil FC | W | 3:12:1 |
| 20.11.1999 | 2. Round | 2. Rd | H | ![]() | Chester City | L | 1:21:1 |