| date | time | team | opposition | venue | type | result | report |
| Saturday, May 8, 1999 | 14:00 | Romsey Town | Fulbourn II | Fulbourn | league | drawn | report |
| Saturday, May 15, 1999 | 14:00 | Romsey Town | Newton II | Newton | league | won | report |
| Saturday, May 29, 1999 | 14:00 | Romsey Town | Foxton II | Foxton | league | won | report |
| Saturday, June 12, 1999 | 14:00 | Romsey Town | Longstowe II | Emmanuel College | league | cancelled | report |
| Saturday, June 19, 1999 | 14:00 | Romsey Town | Audley End II | Emmanuel College | league | won | report |
| Saturday, June 26, 1999 | 14:00 | Romsey Town | Linton II | Linton | league | won | report |
| Saturday, July 3, 1999 | 14:00 | Romsey Town | Cherry Hinton II | Quy | league | won | report |
| Saturday, July 10, 1999 | 14:00 | Romsey Town | Fulbourn II | Emmanuel College | league | won | report |
| Wednesday, July 14, 1999 | 18:00 | Romsey Town | Remnants | Fitzwilliam College | friendly | won | report |
| Saturday, July 17, 1999 | 14:00 | Romsey Town | Foxton II | Emmanuel College | league | won | report |
| Saturday, July 24, 1999 | 14:00 | Romsey Town | Newton II | Emmanuel College | league | won | report |
| Saturday, July 31, 1999 | 14:00 | Romsey Town | Longstowe II | Longstowe | league | lost | report |
| Saturday, August 7, 1999 | 14:00 | Romsey Town | Cherry Hinton II | Emmanuel College | league | cancelled | report |
| Saturday, August 21, 1999 | 14:00 | Romsey Town | Audley End II | Audley End | league | won | report |
| Saturday, September 4, 1999 | 14:00 | Romsey Town | Linton II | Linton | league | won | report |