Lincolnshire Senior Cup 2008-09
Semi-Finals
- Grimsby Town 1-0 Lincoln City
Final (@ Scunthorpe United, 02/08/08)
- Scunthorpe United 4-0 Grimsby Town
Lincolnshire Senior Shield 2008-09
Quarter Finals
- Stamford 4-3 Gainsborough Trinity
- Spalding United 0-2 Boston United
- Grantham Town 2-1 Brigg Town
Semi-Finals
- Boston United 2-0 Lincoln United
- Grantham Town 0-1 Stamford
Final (@ Boston United, 3/12/08)
- Stamford 4-1 Boston United
Lincolnshire County Senior Trophy 2008-09
First Round
- Bottesford Town 1-7 Boston Town
- Holbeach United 2-1 Bourne Town
- Grimsby Borough 2-1 Nettleham
- Lincoln Moorlands Railway 2-1 Barton Town Old Boys
- Blackstones 3-2 Appleby Frodingham
- Sleaford Town 7-2 Harrowby United
Quarter Finals
- Winterton Rangers 3-1 Blackstones
- Deeping Rangers 1-3 Boston Town
- Grimsby Borough 1-3 Lincoln Moorlands Railway
- Sleaford Town 2-1 Holbeach United
Semi-Finals
- Sleaford Town 0-1 Winterton Rangers
- Boston Town 4-0 Lincoln Moorlands Railway
Final (@ Lincoln City, 21/4/09)
- Winterton Rangers 0-2 Boston Town
2008-09 Cups Summary
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