Middlesex Senior Challenge Cup 2005-06
First Round
- Enfield 1-1 Ashford Town (Middx) (Enfield won 8-7 on penalties)
- North Greenford United 0-2 Hayes
- Enfield Town 4-1 Southall
- Northwood 3-1 Ruislip Manor
- Hillingdon Borough 5-1 Wembley
- Wealdstone 1-0 Yeading
- Edgware Town 1-0 Feltham
- Bedfont 0-3 Hampton & Richmond Borough
- Hanwell Town 0-3 Staines Town
- Brentford 4-0 Potters Bar Town
Second Round
- Brook House 2-3 Staines Town
- Harefield United 0-1 Hayes
- Harrow Borough 3-1 Wingate & Finchley
- Hendon 5-4 Wealdstone
- Uxbridge 0-3 Enfield Town
- Northwood 1-0 Enfield
- Edgware Town 6-1 Brentford
- Hampton & Richmond Borough 3-0 Hillingdon Borough
Quarter Finals
- Hayes 2-0 Edgware Town
- Enfield Town 1-2 Hampton & Richmond Borough
- Northwood 2-1 Hendon
- Harrow Borough 4-1 Staines Town
Semi-Finals
- Hampton & Richmond Borough 1-0 Northwood
Final (17th April)
- Hampton & Richmond Borough 0-0 Hayes (@ Harrow Borough, Hampton & Richmond Borough won 4-3 on penalties)
Middlesex Charity Cup 2005-06
First Round
- Brook House 2-1 Edgware Town
- Hanwell Town 0-4 Wingate & Finchley
- Kingsbury Town 5-1 Southall
- Uxbridge 1-0 Northwood
- Bedfont w/o-scr Hampton & Richmond Borough
- Hillingdon Borough 1-1 Ruislip Manor (Ruislip Manor won 4-1 on penalties)
- Harefield United 4-1 Wembley
- Potters Bar Town 4-2 Enfield
Second Round
- Potters Bar Town 1-2 Brentford (@ Brentford)
- Feltham 0-3 Uxbridge
- Harrow Borough 3-2 Yeading
- Kingsbury Town 2-1 North Greenford United
- Bedfont 2-1 Staines Town
- Wealdstone 2-3 Harefield United
- Brook House 0-2 Enfield Town
- Ruislip Manor 2-2 Wingate & Finchley (Wingate & Finchley won 3-2 on penalties)
Quarter Finals
- Enfield Town 2-0 Uxbridge
- Harefield United 3-4 Bedfont
- Kingsbury Town 1-2 Wingate & Finchley
- Brentford scr-w/o Harrow Borough
Semi-Finals
- Enfield Town 0-0 Wingate & Finchley (Enfield Town won 4-2 on penalties)
- Harrow Borough 5-0 Bedfont
Final (25th April)
- Enfield Town 0-2 Harrow Borough (@ Yeading)
2005-06 Cups Summary
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