Wiltshire Premier Shield 2008-09
Semi-Finals
- Chippenham Town 0-1 Swindon Town
- Swindon Town 1-2 Chippenham Town
- Aggregate 2-2, Swindon Town won 5-3 on penalties
- Swindon Supermarine 3-2 Salisbury City
- Salisbury City 3-1 Swindon Supermarine
- Salisbury won 5-4 on aggregate
Final (@ Salisbury City, 29/4/09)
- Salisbury City 3-1 Swindon Town
Wiltshire Senior Cup 2008-09
First Round
- Westbury United 6-0 Cricklade Town
- Purton 2-3 Warminster Town
- Bradford Town 5-1 Wroughton
- Amesbury Town 3-0 Malmesbury Victoria
- F C Chippenham 3-5 Downton
- Westside United 0-8 New College Swindon (@ New College)
- Trowbridge Town 1-2 Bromham
- Pewsey Vale 2-3 Shrewton United
- Marlborough Town 0-1 Wootton Bassett Town
Second Round
- Bemerton Heath Harlequins 1-0 Bradford Town
- Calne Town 3-2 Shrewton United
- Wootton Bassett Town 6-0 Bromham
- Warminster Town 3-2 Devizes Town
- Laverstock & Ford 2-1 New College Swindon
- Melksham Town 5-0 Amesbury Town
- Downton 4-4 Corsham Town (Corsham won 5-4 on penalties)
- Westbury United 2-4 Highworth Town
Quarter Finals
- Bemerton Heath Harlequins 0-3 Highworth Town
- Warminster Town 3-2 Calne Town
- Laverstock & Ford 2-3 Melksham Town
- Wootton Bassett Town 2-1 Corsham Town
Semi-Finals
- Highworth Town 2-1 Melksham Town (@ Highworth Town)
- Warminster Town 2-1 Wootton Bassett Town (@ Melksham Town)
Final (@ Chippenham Town, 22/4/09)
- Highworth Town 2-1 Warminster Town
2008-09 Cups Summary
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