| Date | Competition | Outcome | Home team | Score/Time | Away team | ||
|---|---|---|---|---|---|---|---|
| 31-10-09 | Conference N / S | L |
Hampton & Richmond | 4 - 0 | Maidenhead United | View events | More info |
| 07-11-09 | Conference N / S | D |
Chelmsford City | 1 - 1 | Maidenhead United | View events | More info |
| 14-11-09 | Conference N / S | W |
Maidenhead United | 3 - 2 | Basingstoke Town | View events | More info |
| 21-11-09 | FA Trophy | L |
Maidenhead United | 0 - 1 | Bath City | More info | |
| 28-11-09 | Conference N / S | L |
Havant & Waterlooville | 1 - 0 | Maidenhead United | View events | More info |
| 01-12-09 | Conference N / S | Maidenhead United | PSTP | Braintree Town | More info | ||
| 05-12-09 | Conference N / S | Maidenhead United | 16 : 00 | Lewes | More info | ||
| 12-12-09 | FA Trophy | Bishop's Stortford | 16 : 00 | Maidenhead United | More info | ||
| 19-12-09 | Conference N / S | Worcester City | 16 : 00 | Maidenhead United | More info | ||
| 26-12-09 | Conference N / S | Maidenhead United | 16 : 00 | St Albans City | More info |
| 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 | ||
| 12-12-09 | FA Trophy | Weymouth | 16 : 00 | Salisbury City | More info | ||
| 19-12-09 | Conference N / S | Weymouth | 16 : 00 | Braintree Town | More info |
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