2007-2008
Winners PIONEER FC
Runners up PILL AFC
First Round 6th September 2008
| Pill AFC | 3 | v | 4 | Lliswerry FC |
| Rogerstone AFC | 5 | v | 2 | Albion Rovers |
| Newport Corinthians | 2 | v | 1 | Spencer Boys Club |
| Shaftesbury Youth | 12 | v | 1 | Cromwell Youth |
| Caerleon Town | 2 | v | 3 | Trethomas Bluebirds |
| Pill Mill Hibernians | 4 | v | P | Villa Dino Christchurch |
| Llanwern Sports | 2 | v | 5 | Ship & Pilot FC |
| Lucas Cwmbran | 0 | v | 1 | Malpas FC |
| Tradesmans Arms | 3 | v | 1 | Cwmbran Celtic |
| Oakfield AFC | 3 | v | 1 | Henllys Rangers |
| St Julians AFC | bye | |||
| Pontnewydd United | bye | |||
| Coed Eva Athletic | bye | |||
| Marshfield AFC | bye | |||
| AC Pontymister | bye | |||
| Whiteheads AFC | bye |
Second Round 11th October 2008
|
Lliswerry FC |
3 | v | 2 | Oakfield AFC |
| Tradesmans Arms | 6 | v | 3 | Newport Corinthians |
| Trethomas Bluebirds | 1 | v | 5 | Pill Mill Hibernians |
| Coed Eva Athletic | 5 | v | 2 | Shaftesbury Youth |
| Marshfield AFC | 0 | v | 2 | St Julians AFC |
| Rogerstone AFC | 6 | v | 5 | Malpas FC |
|
Ship & Pilot FC |
17 | v | 1 | Whiteheads AFC |
| Pontnewydd United | 3 | v | 1 | AC Pontymister |
Third Round March 2009
Semi-Final th April 2009
Final May 2009