| 01-Apr-09 | Preliminary Round of the Cup | ||
| 08-Apr-09 | Luddesdowne Cocks | v | Star Meadow Sports |
| Harriers 2 | v | Villager Hurricanes | |
| Sydney Arms | v | Redstart | |
| Hartley Owls | v | Pilot | |
| Lordswood Tempest | v | Beauty of Bath 2 | |
| 15-Apr-09 | Knockout Cup First Round | ||
| 22-Apr-09 | Star Meadow Sports | v | Beauty of Bath 2 |
| Pilot | v | Lordswood Tempest | |
| Redstart | v | Hartley Owls | |
| Villager Hurricanes | v | Sydney Arms | |
| Luddesdowne Cocks | v | Harriers 2 | |
| 29-Apr-09 | Harriers 2 | v | Star Meadow Sports |
| Sydney Arms | v | Luddesdowne Cocks | |
| Hartley Owls | v | Villager Hurricanes | |
| Lordswood Tempest | v | Redstart | |
| Beauty of Bath 2 | v | Pilot | |
| 06-May-09 | Plate Preliminary Round | ||
| 13-May-09 | Star Meadow Sports | v | Pilot |
| Redstart | v | Beauty of Bath 2 | |
| Villager Hurricanes | v | Lordswood Tempest | |
| Luddesdowne Cocks | v | Hartley Owls | |
| Harriers 2 | v | Sydney Arms | |
| 20-May-09 | Sydney Arms | v | Star Meadow Sports |
| Hartley Owls | v | Harriers 2 | |
| Lordswood Tempest | v | Luddesdowne Cocks | |
| Beauty of Bath 2 | v | Villager Hurricanes | |
| Pilot | v | Redstart | |
| 27-May-09 | Star Meadow Sports | v | Redstart |
| Villager Hurricanes | v | Pilot | |
| Luddesdowne Cocks | v | Beauty of Bath 2 | |
| Harriers 2 | v | Lordswood Tempest | |
| Sydney Arms | v | Hartley Owls | |
| 03-Jun-09 | Cup Round 2 / Plate Round 1 | ||
| 10-Jun-09 | Hartley Owls | v | Star Meadow Sports |
| Lordswood Tempest | v | Sydney Arms | |
| Beauty of Bath 2 | v | Harriers 2 | |
| Pilot | v | Luddesdowne Cocks | |
| Redstart | v | Villager Hurricanes | |
| 17-Jun-09 | Cup Round 3 / Plate Round 2 | ||
| 24-Jun-09 | Star Meadow Sports | v | Villager Hurricanes |
| Luddesdowne Cocks | v | Redstart | |
| Harriers 2 | v | Pilot | |
| Sydney Arms | v | Beauty of Bath 2 | |
| Hartley Owls | v | Lordswood Tempest | |
| 01-Jul-09 | Lordswood Tempest | v | Star Meadow Sports |
| Beauty of Bath 2 | v | Hartley Owls | |
| Pilot | v | Sydney Arms | |
| Redstart | v | Harriers 2 | |
| Villager Hurricanes | v | Luddesdowne Cocks | |
| 08-Jul-09 | Star Meadow Sports | v | Luddesdowne Cocks |
| Villager Hurricanes | v | Harriers 2 | |
| Redstart | v | Sydney Arms | |
| Pilot | v | Hartley Owls | |
| Beauty of Bath 2 | v | Lordswood Tempest | |
| 15-Jul-09 | Cup Round 4 / Plate Round 3 | ||
| 22-Jul-09 | Beauty of Bath 2 | v | Star Meadow Sports |
| Lordswood Tempest | v | Pilot | |
| Hartley Owls | v | Redstart | |
| Sydney Arms | v | Villager Hurricanes | |
| Harriers 2 | v | Luddesdowne Cocks | |
| 29-Jul-09 | Star Meadow Sports | v | Harriers 2 |
| Luddesdowne Cocks | v | Sydney Arms | |
| Villager Hurricanes | v | Hartley Owls | |
| Redstart | v | Lordswood Tempest | |
| Pilot | v | Beauty of Bath 2 | |
| 05-Aug-09 | Pilot | v | Star Meadow Sports |
| Beauty of Bath 2 | v | Redstart | |
| Lordswood Tempest | v | Villager Hurricanes | |
| Hartley Owls | v | Luddesdowne Cocks | |
| Sydney Arms | v | Harriers 2 | |
| 12-Aug-09 | Star Meadow Sports | v | Sydney Arms |
| Harriers 2 | v | Hartley Owls | |
| Luddesdowne Cocks | v | Lordswood Tempest | |
| Villager Hurricanes | v | Beauty of Bath 2 | |
| Redstart | v | Pilot | |
| 19-Aug-09 | Redstart | v | Star Meadow Sports |
| Pilot | v | Villager Hurricanes | |
| Beauty of Bath 2 | v | Luddesdowne Cocks | |
| Lordswood Tempest | v | Harriers 2 | |
| Hartley Owls | v | Sydney Arms | |
| 26-Aug-09 | Star Meadow Sports | v | Hartley Owls |
| Sydney Arms | v | Lordswood Tempest | |
| Harriers 2 | v | Beauty of Bath 2 | |
| Luddesdowne Cocks | v | Pilot | |
| Villager Hurricanes | v | Redstart | |
| 02-Sep-09 | postponed matches | ||
| 09-Sep-09 | Villager Hurricanes | v | Star Meadow Sports |
| Redstart | v | Luddesdowne Cocks | |
| PilotRedstart | v | Harriers 2 | |
| Beauty of Bath 2 | v | Sydney Arms | |
| Lordswood Tempest | v | Hartley Owls | |
| 16-Sep-09 | Star Meadow Sports | v | Lordswood Tempest |
| Hartley Owls | v | Beauty of Bath 2 | |
| Sydney Arms | v | Pilot | |
| Harriers 2 | v | Redstart | |
| Luddesdowne Cocks | v | Villager Hurricanes | |