Herts Senior Challenge Cup 2008-09
First Round
- Leverstock Green 4-1 Potters Bar Town
- Hertford Town 2-0 Colney Heath
- Broxbourne Borough V & E 1-2 Hitchin Town
- Welwyn Garden City 1-0 Cockfosters
- St Albans City 3-0 Barnet
- Hemel Hempstead Town 3-3 Bishop's Stortford (Stortford won 4-3 on penalties)
Second Round
- Tring Athletic 1-2 Hertford Town
- Sawbridgeworth Town 1-3 Boreham Wood
- Ware 4-1 Bishop's Stortford
- Leverstock Green 3-0 Watford
- Berkhamsted Town scr-w/o Stevenage Borough
- St Margaretsbury 2-4 St Albans City
- Oxhey Jets 3-1 Welwyn Garden City
- Cheshunt 3-2 Hitchin Town
Quarter Finals
- St Albans City 0-3 Oxhey Jets
- Stevenage Borough 4-2 Hertford Town
- Cheshunt 3-0 Ware
- Boreham Wood 1-3 Leverstock Green
Semi-Finals
- Stevenage Borough 1-0 Leverstock Green
Final (@ HCFA HQ, Letchworth, 8/4/09)
- Cheshunt 1-2 Stevenage Borough
Herts Charity Cup 2008-09
Quarter Finals
- Ware 4-0 Bishop's Stortford
- Potters Bar Town 0-3 Berkhamsted Town
- Hitchin Town 1-4 St Albans City
- Hemel Hempstead Town 2-1 Cheshunt
Semi-Finals
- Berkhamsted Town 2-3 Ware
- Hemel Hempstead Town 10-0 St Albans City
Final (@ HCFA HQ, Letchworth, 18/2/09)
- Ware 1-2 Hemel Hempstead Town
Herts Senior Centenary Trophy 2008-09
First Round
- Bovingdon 2-0 Royston Town
- Standon & Puckeridge 1-3 Met Police Bushey
- Wormley Rovers 6-2 Buntingford Town
- London Colney 1-2 Codicote
- Park Street Village 3-3 Sun Postal Sports (Park Street won 4-3 on penalties)
- Baldock Town Letchworth 1-4 Kings Langley
- Bedmond S & S 0-11 Hatfield Town
Second Round
- Hertford Heath 3-0 Sandridge Rovers
- Knebworth 1-7 Evergreen
- Hoddesdon Town 2-0 Lemsford
- Metropolitan Police Bushey 1-3 Harpenden Town
- Kings Langley 1-2 London Lions
- Wormley Rovers 2-1 Mill End Sports
- Park Street Village 4-1 Codicote
- Bovingdon 4-4 Hatfield Town (Hatfeld won 4-3 on penalties)
Quarter Finals
- Harpenden Town 2-4 Hoddesdon Town
- Evergreen 0-1 Park Street Village
- London Lions 0-0 Wormley Rovers (London Lions won 4-1 on penalties)
- Hertford Heath 2-5 Hatfield Town
Semi-Finals
- Park Street Village 1-2 Hatfield Town
- Hoddesdon Town 3-2 London Lions
Final (@ HCFA HQ, Letchworth, 25/3/09)
- Hatfield Town 1-1 Hoddesdon Town (Hoddesdon won 5-3 on penalties)
Herts Charity Shield 2008-09
First Round
- London Colney 1-2 Colney Heath
- Sawbridgeworth Town 1-2 Broxbourne Borough V & E
- Leverstock Green 4-5 Royston Town
- Oxhey Jets 5-0 Welwyn Garden City
- Hertford Town 2-4 Tring Athletic
- Kings Langley 1-0 St Margaretsbury
- Harpenden Town 1-3 Hoddesdon Town
- Hatfield Town 2-5 Sun Postal Sports (@ Hertford Town)
Quarter Finals
- Oxhey Jets 2-4 Royston Town
- Sun Postal Sports 1-3 Kings Langley
- Hoddesdon Town 0-2 Broxbourne Borough V & E
- Colney Heath 3-4 Tring Athletic
Semi-Finals
- Broxbourne Borough V & E 3-2 Kings Langley
- Royston Town 5-4 Tring Athletic
Final (@ HCFA HQ, Letchworth, 12/5/09)
- Broxbourne Borough V & E 4-1 Royston Town
2008-09 Cups Summary
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