First Round Saturday 13th November 2010
| Pontnewydd United | 5 | v | 2 | CCYP AFC |
| Pill Hibernians | 2 | v | 1 | Cwmbran Celtic |
| Bettws Socialdad | 6 | v | 0 | Shaftesbury Youth |
| Ty-Sign AFC | 0 | v | 4 | Lliswerry AFC 2nds |
| Caerleon Town | 1 | v | 6 | Pill AFC |
| Ponthir AFC | 0 | v | 2 | Lucas Cwmbran |
| Villa Dino Christchurch | 7 | v | 5 | Newport Eagles 1sts |
| Bettws Social Club | 7 | v | 3 | Racing Club Newport |
Byes
| Lliswerry AFC 3rds | Albion Rovers 2nds | |||
| Coed Eva Athletic | Newport Eagles 2nds | |||
| Riverside Tavern | F.C.Pockets AFC | |||
| Rogerstone AFC 2nds | Gaer Park Rangers |
Second Round Saturday 13th February 2011
| Rogerstone AFC | v | Albion Rovers | ||
| Bettws Socialdad | v | Pill Hibernians | ||
| Gaer Park Rangers | v | Villa Dino Christchurch | ||
| F C Pockets | v | Lliswerry AFC | ||
| Pill AFC | v | Pontnewydd United | ||
| Lliswerry AFC | v | Coed Eva Athletic | ||
| Lucas Cwmbran | v | Riverside Tavern | ||
| Newport Eagles | v | Bettws Social Club |