Dorset Senior Cup 2005-06
First Round
- Barwick & Stoford 1-4 Wareham Rangers
- Corfe Mullen United 4-2 Dorchester United
- Blandford United 0-1 Gillingham Town
- Easton United 3-1 Cranborne
- Witchampton United 0-6 Holt United
Second Round
- Allendale 1-0 Easton United
- Sturminster Marshall 0-4 Chickerell United
- Wareham Rangers 1-4 Poole Borough
- Holt United 2-0 Swanage Town & Herston
- Weymouth United 2-0 Sturminster Newton United
- St Pauls (Jersey) 4-1 Cobham Sports
- Bournemouth Sports 2-3 Gillingham Town
- Hamworthy Recreation 2-1 Stourpaine
- Corfe Mullen United 2-6 Sherborne Town
Third Round
- Verwood Town 1-1 Portland United (abandoned 90 minutes)
- Poole Borough 3-1 St Pauls (Jersey)
- Allendale 1-4 Chickerell United
- Holt United 3-2 Shaftesbury
- Bridport 0-0 Hamworthy United
- Sherborne Town 6-0 Weymouth United
- Hamworthy United 3-0 Bridport
- Wimborne Town 1-2 Poole Town
Third Round Replays
- Hamworthy United 3-0 Bridport
- Portland United 0-2 Verwood Town
Quarter Finals
- Gillingham Town 2-0 Sherborne Town
- Chickerell United 1-2 Verwood Town
- Holt United 1-3 Hamworthy United
- Poole Town 2-1 Poole Borough
Semi-Finals
- Gillingham Town 1-2 Poole Town (@ Shaftesbury)
- Hamworthy United 2-1 Verwood Town (@ Wimborne Town)
Final (19th April)
- Poole Town 1-2 Hamworthy United (@ Wimborne Town)
2005-06 Cups Summary
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