Middlesex Senior Challenge Cup 2008-09
First Round
- Wembley 5-2 Tokyngton Manor
- Enfield Town 2-1 Wingate & Finchley
- Ashford Town (Middlesex) 2-1 North Greenford United
- Hillingdon Borough 2-8 Hayes & Yeading United
- Staines Town 5-0 Enfield 1893
Second Round
- A F C Hayes 6-0 Uxbridge
- Hendon 3-0 Bedfont Green
- Harefield United 1-0 Hayes & Yeading United
- Bedfont 0-4 Staines Town
- Hanwell Town 2-3 Ashford Town (Middlesex)
- Harrow Borough 6-2 Enfield Town
- Hampton & Richmond Borough 1-0 Northwood
- Wealdstone 3-0 Wembley
Quarter Finals
- Harefield United 2-4 A F C Hayes
- Wealdstone 1-0 Hampton & Richmond Borough
- Hendon 1-1 Harrow Borough (Hendon won 2-1 on penalties)
- Staines Town 1-2 Ashford Town (Middlesex)
Semi-Finals
- Ashford Town (Middlesex) 1-4 A F C Hayes
Final (@ Northwood, 13/4/09)
Middlesex Charity Cup 2008-09
First Round
- Northwood - North Greenford United
- Wealdstone - A F C Hayes
- Wingate & Finchley - Harrow Borough (@ Harrow Borough)
- Bedfont 3-1 Hanwell Town
- Harefield United - Uxbridge
Quarter Finals
- Enfield Town - Wealdstone or AFC Hayes
- Northwood or N Greenford U - Hillingdon Borough
- Harefield U or Uxbridge - Wembley
- Bedfont or Hanwell T - Wingate & F or Harrow Bor
At this point, the competition was abandoned for the 2008-09 season
2008-09 Cups Summary
Please credit the F.C.H.D. when using this information elsewhere