Nottinghamshire Senior Cup 2008-09
First Round
- Teversal 1-1 Greenwood Meadows (Greenwood Meadows won 4-2 on penalties)
- Clipstone Welfare 1-1 Boots Athletic (Clipstone won 3-2 on penalties)
- Blidworth Welfare 2-1 Bilborough Pelican
- Sutton Town 1-1 Newark Flowserve (Newark won 3-2 on penalties)
- Kimberley Town 2-1 Rolls Royce Leisure
- Wollaton 4-2 Attenborough
- Forest Town 7-0 Thoresby Colliery Welfare
- Radcliffe Olympic 3-1 Caribbean Cavaliers
- Dunkirk 1-0 Newark Town
- Nottinghamshire Police 2-1 Keyworth United
- Radford 0-1 Hucknall Rolls Leisure
- Basford United 2-3 Calverton Miners Welfare
Second Round
- Newark Flowserve 1-3 Hucknall Rolls Leisure
- Blidworth Welfare 1-3 Radcliffe Olympic
- Greenwood Meadows 2-3 Dunkirk
- Kimberley Town 0-2 Forest Town
- Nottinghamshire Police 1-4 Calverton Miners Welfare
- Wollaton 2-0 Clipstone Welfare
Third Round
- Wollaton 2-3 Arnold Town (@ Radford)
- Hucknall Rolls Leisure 0-4 Carlton Town
- Southwell City 1-7 Eastwood Town
- Gedling Town 3-1 Gedling Miners Welfare
- Dunkirk 0-1 Hucknall Town (awarded to Dunkirk)
- Ollerton Town 1-2 Rainworth Miners Welfare
- Calverton Miners Welfare 0-4 Retford United
- Forest Town 3-0 Radcliffe Olympic
Quarter Finals
- Rainworth Miners Welfare 0-1 Eastwood Town
- Carlton Town 3-0 Forest Town
- Retford United 1-0 Dunkirk
- Gedling Town 1-2 Arnold Town
Semi-Finals
- Retford United 4-0 Arnold Town
- Eastwood Town 3-1 Carlton Town
Final (@ Notts County, 7/5/09)
- Retford United 2-1 Eastwood Town
2008-09 Cups Summary
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