Dorset Senior Cup 2008-09
First Round
- Portland United 4-2 Sturminster Marshall
- Holt United 4-0 Verwood Town
- Shaftesbury 4-1 Poole Borough
- Bridport 3-2 Cobham Sports
Second Round
- Dorchester Town 4-0 Blandford United
- Portland United 0-2 Hamworthy United
- Sturminster Newton United 0-1 Gillingham Town
- Wimborne Town 5-0 Hamworthy Recreation
- Bridport w/o-scr Cranborne
- Holt United 1-3 Sherborne Town
- Swanage Town & Herston 0-5 Poole Town
- Chickerell United 3-0 Shaftesbury
Quarter Finals
- Hamworthy United 0-2 Poole Town
- Dorchester Town 2-0 Bridport
- Wimborne Town 6-1 Gillingham Town
- Chickerell United 0-2 Sherborne Town
2008-09 Cups Summary
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