Herts Senior Challenge Cup 2005-06
First Round
- Royston Town 1-3 Watford
- Cheshunt 0-1 Hertford Town
- Berkhamsted Town 1-2 Bishops Stortford
- Harpenden Town 2-5 Broxbourne Borough V & E
- Hitchin Town 2-3 Hemel Hempstead Town
- Welwyn Garden City 3-1 Sawbridgworth Town
- Ware 1-2 St Margaretsbury
Second Round
- Hemel Hempstead Town 6-1 St Albans City
- London Colney 0-1 Welwyn Garden City
- Potters Bar Town 1-3 Bishop's Stortford
- Broxbourne Borough V & E 3-4 Stevenage Borough
- Tring Town 1-0 Watford
- Leverstock Green 1-1 Hertford Town (Leverstock Green won 4-2 on penalties)
- St Margaretsbury 0-6 Boreham Wood
- Oxhey Jets 2-1 Barnet
Quarter Finals
- Stevenage Borough 5-0 Tring Athletic
- Oxhey Jets 2-1 Hemel Hempstead Town
- Bishop's Stortford 4-3 Welwyn Garden City
- Leverstock Green 1-1 Boreham Wood (Boreham Wood won 4-3 on penalties)
Semi-Finals
- Stevenage Borough 2-1 Boreham Wood
- Oxhey Jets 2-3 Bishop's Stortford
Final (@ County Ground, Letchworth, 4th April)
- Bishop's Stortford 1-0 Stevenage Borough
Herts Charity Cup 2005-06
First Round
- Hertford Town 1-4 Cheshunt
- Berkhamstead Town 3-2 Hitchin Town
Quarter Finals
- Potters Bar Town 3-1 Bishop's Stortford
- St Albans City scr-w/o Boreham Wood
- Ware 1-2 Hemel Hempstead Town
- Cheshunt 3-1 Berkhamsted Town
Semi-Finals
- Cheshunt 2-0 Potters Bar Town
- Hemel Hempstead Town 2-3 Boreham Wood
Final (@ County Ground, Letchworth, 25th April)
- Boreham Wood 0-1 Cheshunt
Herts Senior Centenary Trophy 2005-06
First Round
- Evergreen 4-2 Whitewebbs
- Metropolitan Police Bushey 0-1 Hadley
- Bushey Rangers 1-0 Colney Heath
- Hinton 2-5 Wormley Rovers
Second Round
- Kentish Town 1-4 Codicote
- Sun Postal Sports 0-3 Hatfield Town
- Bedmond Sports & Social 3-2 Buntingford Town
- Hoddesdon Town 2-0 Chipperfield Corinthians
- Hadley 4-1 Little Munden
- Sandridge Rovers 1-2 Elliott Star
- Wormley Rovers 1-2 London Lions
- Evergreen 2-3 Bushey Rangers
Quarter Finals
- Hoddesdon Town 1-0 Hadley
- London Lions 0-2 Codicote
- Bedmond Sports & Social 3-1 Hatfield Town
- Bushey Rangers 2-1 Elliott Star
Semi-Finals
- Bedmond 0-2 Hoddesdon Town
- Codicote 4-1 Bushey Rangers
Final (@ County Ground, Letchworth, 28th March)
- Codicote 2-0 Hoddesdon Town
Herts Charity Shield 2005-06
First Round
- Tring Athletic 2-0 Oxhey Jets
- Sawbridgeworth Town 3-0 Metropolitan Police Bushey
- Broxbourne Borough V & E 1-2 Hoddesdon Town
- London Colney 2-1 Colney Heath
- Royston Town 0-1 St Margaretsbury
- Leverstock Green 2-1 Hadley
- Hatfield Town 1-0 Welwyn Garden City (@ Welwyn GC)
- Harpenden Town 1-0 Kings Langley
Quarter Finals
- Hoddesdon Town 2-5 Sawbridgeworth Town
- Tring Athletic 0-2 Leverstock Green
- St Margaretsbury 2-1 Harpenden Town
- London Colney 3-0 Hatfield Town
Semi-Finals
- Sawbridgeworth Town 2-0 Leverstock Green
- London Colney 3-1 St Margaretsbury
Final (@ County Ground, Letchworth, 19th April)
- London Colney 1-2 Sawbridgeworth Town
2005-06 Cups Summary
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