2007-2008
Winners SPENCER OLD BOYS
Runners up RIVERVIEW HIBERNIANS
First Round September 6th 2008
| Graig-Y-Rhacca 2nds | 4 | v | 5 | County Athletic |
| Ship & Pilot FC 2nds | 9 | v | 1 | Malpas Gladiator 2nds |
| Riverview Hibernians | 4 | v | 0 | Caerleon Town 2nds |
| Bettws Social Club 1st | 4 | v | 2 | Oakfield AFC 2nds |
| Lliswerry FC 2nds | 3 | v | 4 | Graig-Y-Rhacca 1st |
| Cwmcarn Athletic 2nds | 4 | v | 2 | Rogerstone 2nds |
| Albion Rovers 3rds | 1 | v | 7 | Spencer Old Boys |
| Albion Rovers 2nds | bye | |||
| Racing Club Npt 2nds | bye | |||
| Malpas FC 3rds | bye | |||
| Cwmbran Celtic 2nds | bye | |||
| Pill AFC 3rds | bye | |||
| Bettws Social Club 2nds | bye | |||
| Ty-Sign AFC | bye | |||
| Malpas FC 2nds | bye | |||
| Marshfield AFC 2nds | bye | |||
| Cwmcarn Athletic 1st | bye | |||
| Ponthir | bye | |||
| Newport Eagles | bye | |||
| Tredegar Arms | bye | |||
| Cwmbran Centre YP | bye | |||
| Pill Mill Hibernians 2nds | bye | |||
| Pontnewydd Utd 2nds | bye | |||
| Malpas Gladiator 1st | bye | |||
| AC Pontymister 2nds | bye | |||
| Pill AFC 2nds | bye | |||
| Lliswerry FC 3rds | bye | |||
| Coed Eva Athletic 2nds | bye | |||
| Malpas United | bye | |||
| Racing Club Npt 1st | bye | |||
| Crows Nest AFC | bye | |||
| Gaer Park Rangers | bye |
Second Round 11th October 2008
| Crows Nest AFC | 3 | v | 10 | Malpas United |
| Marshfield AFC 2nds | 1 | v | 4 | Coed Eva Athletic 2nds |
| Tredegar Arms | 3 | v | 6 | Ship & Pilot FC 2nds |
| Bettws Social Club 1st | 5 | v | 1 | Malpas Gladiator 1st |
| Pill Mill Hibernians 2nds | 1 | v | 4 | Albion Rovers 2nds |
| Malpas FC 2nds | 1 | v | 6 | County Athletic |
| Cwmbran Centre YP | 8 | v | 7 | Pontnewydd Utd 2nds |
| Pill AFC 3rds | 2 | v | 1 | Spencer OB |
| Cwmbran Celtic 2nds | P | v | P | Pill AFC 2nds |
| Riverview Hibernians | 3 | v | 0 | Bettws Social Club 2nds |
| Newport Eagles | 0 | v | 23 | Ponthir |
| Ty-Sign AFC | 1 | v | 0 | Graig Y Rhacca 1st |
| Racing Club Npt 2nds | 2 | v | 0 | Cwmcarn Athletic 2nds |
| Lliswerry FC 3rds | 2 | v | 5 | Gaer Park Rangers |
| Cwmcarn Athletic 1st | 3 | v | 0 | AC Pontymister 2nds |
| Newport Corries 2nds | 3 | v | 5 | Racing Club Npt 1st |
Third Round March
Fourth Round March
Semi-Finals April th 2009
Final April th 2009