| Date | Competition | Outcome | Home team | Score/Time | Away team | ||
|---|---|---|---|---|---|---|---|
| 27-10-09 | Conference N / S | L |
Weymouth | 0 - 2 | Bath City | View events | More info |
| 31-10-09 | Conference N / S | L |
St Albans City | 2 - 1 | Weymouth | View events | More info |
| 14-11-09 | Conference N / S | W |
Bishop's Stortford | 0 - 1 | Weymouth | View events | More info |
| 17-11-09 | Conference N / S | D |
Weymouth | 0 - 0 | Woking | More info | |
| 21-11-09 | FA Trophy | W |
Weymouth | 3 - 0 | Dorchester Town | More info | |
| 28-11-09 | Conference N / S | Weymouth | PSTP | Staines Town | More info | ||
| 02-12-09 | Conference N / S | Eastleigh | 20 : 45 | Weymouth | More info | ||
| 05-12-09 | Conference N / S | Braintree Town | 16 : 00 | Weymouth | More info | ||
| 19-12-09 | Conference N / S | Weymouth | 16 : 00 | Braintree Town | More info | ||
| 26-12-09 | Conference N / S | Dorchester Town | 16 : 00 | Weymouth | More info |
| Date | Competition | Outcome | Home team | Score/Time | Away team | ||
|---|---|---|---|---|---|---|---|
| 31-10-09 | Conference N / S | L |
Dorchester Town | 1 - 3 | Dover Athletic | View events | More info |
| 07-11-09 | Conference N / S | W |
Havant & Waterlooville | 0 - 1 | Dorchester Town | View events | More info |
| 10-11-09 | Conference N / S | L |
Dorchester Town | 1 - 2 | Eastleigh | View events | More info |
| 14-11-09 | Conference N / S | D |
Dorchester Town | 1 - 1 | Worcester City | View events | More info |
| 21-11-09 | FA Trophy | L |
Weymouth | 3 - 0 | Dorchester Town | More info | |
| 28-11-09 | Conference N / S | Woking | 16 : 00 | Dorchester Town | More info | ||
| 01-12-09 | Conference N / S | Dorchester Town | 20 : 45 | Lewes | More info | ||
| 05-12-09 | Conference N / S | Dorchester Town | 16 : 00 | Hampton & Richmond | More info | ||
| 19-12-09 | Conference N / S | Chelmsford City | 16 : 00 | Dorchester Town | More info | ||
| 26-12-09 | Conference N / S | Dorchester Town | 16 : 00 | Weymouth | More info |