| Division A | 29th Oct | Division B | ||||
| Hartley Romans | v | George | Villager B | v | Tovil Titans | |
| Sherwood Oak | v | Villager A | Mossy's People | v | Hartley Centurions | |
| Fighting Cocks | v | Ryarsh | Star Meadow | v | Hartley Friends | |
| Crossover Game: | Lordswood Moldavians | v | Hartley Countrymen | |||
| Division A | 5th Nov | Division B | ||||
| Villager A | v | Fighting Cocks | Hartley Centurions | v | Star Meadow | |
| George | v | Sherwood Oak | Tovil Titans | v | Mossy's People | |
| Hartley Countrymen | v | Hartley Romans | Lordswood Moldavians | v | Villager B | |
| Crossover Game: | Hartley Friends | v | Ryarsh | |||
| Division A | 12th Nov | Division B | ||||
| Sherwood Oak | v | Hartley Countrymen | Mossy's People | v | Lordswood Moldavians | |
| Fighting Cocks | v | George | Star Meadow | v | Tovil Titans | |
| Ryarsh | v | Villager A | Hartley Friends | v | Hartley Centurions | |
| Crossover Game: | Villager B | v | Hartley Romans | |||
| Division A | 19th Nov | Division B | ||||
| George | v | Ryarsh | Tovil Titans | v | Hartley Friends | |
| Hartley Countrymen | v | Fighting Cocks | Lordswood Moldavians | v | Star Meadow | |
| Hartley Romans | v | Sherwood Oak | Villager B | v | Mossy's People | |
| Crossover Game: | Hartley Centurions | v | Villager A | |||
| Division A | 26th Nov | Division B | ||||
| Fighting Cocks | v | Hartley Romans | Star Meadow | v | Villager B | |
| Ryarsh | v | Hartley Countrymen | Hartley Friends | v | Lordswood Moldavians | |
| Villager A | v | George | Hartley Centurions | v | Tovil Titans | |
| Crossover Game: | Mossy's People | v | Sherwood Oak | |||
| Division A | 3rd Dec | Division B | ||||
| Hartley Countrymen | v | Villager A | Lordswood Moldavians | v | Hartley Centurions | |
| Hartley Romans | v | Ryarsh | Villager B | v | Hartley Friends | |
| Sherwood Oak | v | Fighting Cocks | Mossy's People | v | Star Meadow | |
| Crossover Game: | Tovil Titans | v | George | |||
| Division A | 10th Dec | Division B | ||||
| Ryarsh | v | Sherwood Oak | Hartley Friends | v | Mossy's People | |
| Villager A | v | Hartley Romans | Hartley Centurions | v | Villager B | |
| George | v | Hartley Countrymen | Tovil Titans | v | Lordswood Moldavians | |
| Crossover Game: | Star Meadow | v | Fighting Cocks | |||
| 17th Dec 2008 - break |
| 24th Dec 2008 - break |
| 31st Dec 2008 - break |
| 7th Jan 2009 - break |
| 14th Jan 2009 - Cup/Plate last 7 teams reduced to 4 in each |
| Division A | 21st Jan | Division B | ||||
| George | v | Hartley Romans | Lordswood Moldavians | v | Mossy's People | |
| Villager A | v | Sherwood Oak | Tovil Titans | v | Star Meadow | |
| Ryarsh | v | Fighting Cocks | Hartley Centurions | v | Hartley Friends | |
| Crossover Game: | Hartley Countrymen | v | Villager B | |||
| Division A | 28th Jan | Division B | ||||
| Fighting Cocks | v | Villager A | Hartley Friends | v | Tovil Titans | |
| Sherwood Oak | v | George | Star Meadow | v | Lordswood Moldavians | |
| Hartley Romans | v | Hartley Countrymen | Mossy's People | v | Villager B | |
| Crossover Game: | Ryarsh | v | Hartley Centurians | |||
| Division A | 4th Feb | Division B | ||||
| Hartley Countrymen | v | Sherwood Oak | Villager B | v | Star Meadow | |
| George | v | Fighting Cocks | Lordswood Moldavians | v | Hartley Friends | |
| Villager A | v | Ryarsh | Tovil Titans | v | Hartley Centurions | |
| Crossover Game: | Hartley Romans | v | Mossy's People | |||
| Division A | 11th Feb | Division B | ||||
| Ryarsh | v | George | Hartley Centurions | v | Lordswood Moldavians | |
| Fighting Cocks | v | Hartley Countrymen | Hartley Friends | v | Villager B | |
| Sherwood Oak | v | Hartley Romans | Star Meadow | v | Mossy's People | |
| Crossover Game: | Villager A | v | Tovil Titans | |||
| 18th Feb 2009 - Cup/Plate Semi-Finals |
| Division A | 25th Feb | Division B | ||||
| Hartley Romans | v | Fighting Cocks | Mossy's People | v | Hartley Friends | |
| Hartley Countrymen | v | Ryarsh | Villager B | v | Hartley Centurions | |
| George | v | Villager A | Lordswood Moldavians | v | Tovil Titans | |
| Crossover Game: | Sherwood Oak | v | Star Meadow | |||
| Division A | 4th Mar | Division B | ||||
| Villager A | v | Hartley Countrymen | Tovil Titans | v | Villager B | |
| Ryarsh | v | Hartley Romans | Hartley Centurions | v | Mossy's People | |
| Fighting Cocks | v | Sherwood Oak | Hartley Friends | v | Star Meadow | |
| Crossover Game: | George | v | Lordswood Moldavians | |||
| Division A | 11th Mar | Division B | ||||
| Sherwood Oak | v | Ryarsh | Star Meadow | v | Hartley Centurions | |
| Hartley Romans | v | Villager A | Mossy's People | v | Tovil Titans | |
| Hartley Countrymen | v | George | Villager B | v | Lordswood Moldavians | |
| Crossover Game: | Fighting Cocks | v | Hartley Friends | |||
| 13th Mar 2009 - Cup/Plate Finals (neutral venue) |