First Round Saturday 5th December 2009
| K2 - 2 | 4 | v | 6 | Pill AFC |
| Racing Club Newport | 1 | v | 2 | Albion Rovers |
| Ferns AFC | 3 | v | 1 | Sporting Baneswell Social |
| FC Llanyravon | 9 | v | 0 | Caerleon Town |
| Lucas Cwmbran | 7 | v | 6 | Newport Eagles |
| Coed Eva Athletic | 0 | v | 5 | Marshfield |
| Cwmbran Celtic | 3 | v | 1 | Cwmcaen Athletic |
| Ty-Sign AFC | Bye | |||
| Bettws Social Club | Bye | |||
| Lliswerry AFC | Bye | |||
| County Athletic | Bye | |||
| Cromwell Youth | Bye | |||
| Newport Eagles | Bye | |||
| Marshfield | Bye | |||
| Rogerstone AFC | Bye | |||
| CCYP AFC | Bye |
Second Round Saturday 6th March 2010
| Ferns AFC | 1 | v | 4 | Pill AFC 2nds |
| Marshfield 3rds | 0 | v | 7 | Albion Rovers 3rds |
| Cromwell Youth 2nds | 0 | v | 5 | Ty-Sign AFC |
| FC Llanyravon | 0 | v | 3 | Lliswerry AFC 2nds |
| CCYP AFC | 4 | v | 3 | Lucas Cwmbran 2nds |
| Newport Eagles 2nds | 1 | v | 4 | Cwmbran Celtic 2nds |
| Bettws Social Club 2nds | 3 | v | 2 | Rogerstone AFC 2nds |
| Marshfield 2nds | 5 | v | 6 | County Athletic |
Third Round Saturday 27th March 2010
| County Athletic | 2 | v | 3 | Ty-Sign AFC 2nds |
| Pill AFC | 4 | v | 1 | Cwmbran Celtic 2nds |
| Albion Rovers 3rds | 4 | v | 5 | Bettws Social Club 1st |
| CCYP AFC or | 2 | v | 3 | Lliswerry AFC 2nds |
Semi-Final Tuesday April 13th 2010
| Bettws Social Club 1st | 4 | v | 1 | Ty-Sign AFC 2nds |
| Pill AFC | 2 | v | 4 | Lliswerry AFC 2nds |
Final Tuesday April 27th 2010
| Bettws Social Club 1st | 10 | v | 9 | Lliswerry AFC 2nds |
After Extra Time & Penalties