Round Two (played 11 December 2023)
Sponsored by Eddie White of West Moors X
| FERNDOWN RBL | beat | CRICKETERS ALL STARS |
| PADDOCKS | beat | CSSC B |
| CSSC C | beat | GREEN MAN A |
| GREEN MAN B | beat | BARLEY MOWERS |
| WINTON LIBERAL | beat | ST IVES WARRIORS |
| PT&L A | beat | SHOULDER OF MUTTON A |
| WITCHAMPTON WITCHES | beat | ST IVES A |
| CORFE MULLEN RBL | beat | STOCK CUBES |
| WEST MOORS B | beat | RED LION |
| BEARWOOD | beat | DORSET SOLDIER B |
| CRICKETERS HYENAS | beat | CRANBORNE |
| UP THE CRICKS | beat | WIMBORNE FOOTBALL CLUB |
| DORSET SOLDIER A | beat | CRICKETERS TIGERS |
| SHOULDER OF MUTTON D | beat | GREEN MAN C |
| WEST MOORS X | beat | OWLS NEST B |
| CSSC A | beat | SHOULDER OF MUTTON B |