Sunday 5th October 2008 - Round 1

• Match 1 - Handsworth Town 7 - 0 Circle
• Match 2 - Alum Rock P v P West Heath United
• Match 3 - Racing Blythe Galaxy P v P GB Rangers
• Match 4 - Hall Green Bulls Head 0 v 10 Redwood Rangers
• Match 5 - FC Gosta P v P AG Athletic
• Match 6 - Linden Athletic P v P Exeter Rovers
• Match 7 - Sporting Brockhurst 3 v 5 Hockley Heath
• Match 8 - Berkley 3 v 1 Yardley Rovers
• Match 9 - St.George Rangers 0 v 5 Kingshurst St.George
• Match 10 - TR2000 7 v 2 Custard House

Byes -  Pershore Argyle, Chemsley Wood United, Sporting Kingfisher, Garretts Green, College Arms, Stechford Social

Sunday 2nd November 2008 - Round 1

• Match 2 - West Heath United 2 (4) v 2 (3) Alum Rock
• Match 3 - Racing Blythe Galaxy P v P GB Rangers
• Match 5 - FC Gosta P v P AG Athletic
• Match 6 - Linden Athletic 3 v 1 Exeter Rovers

Sunday 9th November 2008 - Round 1

• Match 3 - GB Rangers 3 v 1 Racing Blythe Galaxy
• Match 5 - AG Athletic 2 v 4 FC Gosta

Sunday 23rd November 2008 - Round 2

• Match A - Pershore Argyle P v P Handsworth Town
• Match B - Chemsley Wood United P v P West Heath United
• Match C - Sporting Kingfisher P v P GB Rangers
• Match D - Garretts Green 2 v 10 Redwood Rangers
• Match E - College Arms 2 v 3 FC Gosta
• Match F - Stechford Social P v P Linden Athletic
• Match G - Hockley Heath P v P Berkley
• Match H - Kingshurst St.George P v P TR2000

Sunday 4th January 2009 - Round 2

• Match A - Pershore Argyle v Handsworth Town
• Match B - Chemsley Wood United v West Heath United
• Match C - Sporting Kingfisher v GB Rangers
• Match F - Linden Athletic v Stechford Social
• Match G - Berkley v Hockley Heath
• Match H - Kingshurst St.George v TR2000

Sunday 1st February 2009 - Quarter Finals

• Winner of Match A v Winner of Match B
• Winner of Match C v Redwood Rangers
• FC Gosta v Winner of Match F
• Winner of Match G v Winner of Match H

A draw for the Semi-Final fixtures will be made on completion of the Quarter Final matches.