| Date | Team | Opposition | Venue | Result |
| Saturday, May 8, 1999 | Romsey Town | Fulbourn II | Fulbourn | did not reach a result |
| Saturday, May 15, 1999 | Romsey Town | Newton II | Newton | won by 5 wickets |
| Saturday, May 29, 1999 | Romsey Town | Foxton II | Foxton | won by 8 wickets |
| Saturday, June 12, 1999 | Romsey Town | Longstowe II | Emmanuel College | did not reach a result |
| Saturday, June 19, 1999 | Romsey Town | Audley End II | Emmanuel College | won by 9 wickets |
| Saturday, June 26, 1999 | Romsey Town | Linton II | Linton | won by 8 wickets |
| Saturday, July 3, 1999 | Romsey Town | Cherry Hinton II | Quy | won by 65 runs |
| Saturday, July 10, 1999 | Romsey Town | Fulbourn II | Emmanuel College | won by 55 runs |
| Wednesday, July 14, 1999 | Romsey Town | Remnants | Fitzwilliam College | won by 6 wickets |
| Saturday, July 17, 1999 | Romsey Town | Foxton II | Emmanuel College | won by 7 wickets |
| Saturday, July 24, 1999 | Romsey Town | Newton II | Emmanuel College | won by 8 wickets |
| Saturday, July 31, 1999 | Romsey Town | Longstowe II | Longstowe | lost by 7 wickets |
| Saturday, August 7, 1999 | Romsey Town | Cherry Hinton II | Emmanuel College | did not reach a result |
| Saturday, August 21, 1999 | Romsey Town | Audley End II | Audley End | won by 9 wickets |
| Saturday, September 4, 1999 | Romsey Town | Linton II | Linton | won by 25 runs |