| 07 May 1995 | First Round | Brigg Town v Broughton | Sir John Nelthorpe School, Brigg | Results |
| 07 Jun 1995 | Second Round | Broughton v Bottesford Town | Recreation Ground, Broughton | Results |
| 16 Jul 1995 | Quarter-Final | Broughton v Messingham | Recreation Ground, Broughton | Results |
| 14 May 1995 | First Round | Scunthorpe Town Second XI v Cleethorpes Third XI | Heslam Park, Scunthorpe | Results |
| 14 May 1995 | First Round | Caistor Town v Market Rasen | Brigg Road Ground, Caistor | Results |
| 14 May 1995 | First Round | Southcliffe St Andrews v Bracebridge Heath | Sobraon Barracks, Lincoln | Results |
| 14 May 1995 | First Round | Owmby v Normanby Park Works | Todmoor, Owmby by Spital | Results |
| 14 May 1995 | First Round | Kirton Lindsey v Belton | Redbourne Mere, Kirton in Lindsey | Results |
| 14 May 1995 | First Round | Louth v Skegness | London Road, Louth | Results |
| 14 May 1995 | First Round | Bottesford Town v Outcasts | Birch Park, Bottesford | Results |
| 14 May 1995 | First Round | Keelby v Messingham | Keelby Sports Ground, Keelby | Results |
| 14 May 1995 | First Round | Rustons v Hartsholme | Newark Road, Lincoln | Results |
| 14 May 1995 | First Round | South Kelsey v Nettleton Mines | Waddingham Road, South Kelsey | Results |
| 14 May 1995 | First Round | Alford v Hykeham | Train Fen Holt, Alford | Results |
| 14 May 1995 | First Round | Haxey v Grimsby Town | Haxey Lane, Haxey | Results |
| 30 Apr 1995 | First Round | Lincoln Claytons Second XI v Alkborough | Clayton's Sports Club Ground, Lincoln | Results |
| 30 Apr 1995 | First Round | Barton Town Second XI v Normanby Park | Marsh Lane, Barton on Humber | Results |
| 14 May 1995 | First Round | Grimsby British Rail Sports Association v Nettleham | Carr Lane, Grimsby | Results |
| 12 Jun 1995 | Second Round | Alford v Cleethorpes Third XI | Train Fen Holt, Alford | Results |
| 12 Jun 1995 | Second Round | Messingham v Nettleham | Memorial Playing Field, Messingham | Results |
| 12 Jun 1995 | Second Round | Grimsby Town v not known | Augusta Street, Grimsby | Results |
| 12 Jun 1995 | Second Round | Market Rasen v Normanby Park Works | Rase Park, Market Rasen | Results |
| 12 Jun 1995 | Second Round | Louth v South Kelsey | London Road, Louth | Results |
| 12 Jun 1995 | Second Round | Belton v Normanby Park | Church Street, Belton | Results |
| 12 Jun 1995 | Second Round | Alkborough v Hartsholme | West Halton Lane, Alkborough | Results |
| 10 Jul 1995 | Quarter-Final | Alkborough v Alford | West Halton Lane, Alkborough | Results |
| 10 Jul 1995 | Quarter-Final | Market Rasen v Normanby Park | Rase Park, Market Rasen | Results |
| 10 Jul 1995 | Quarter-Final | not known v Grimsby Town | not known | Results |
| 31 Jul 1995 | Semi-Final | Alford v Market Rasen | Train Fen Holt, Alford | Results |
| 31 Jul 1995 | Semi-Final | Grimsby Town v Messingham | Augusta Street, Grimsby | Results |
| 13 Aug 1995 | Final | Alford v Messingham | Augusta Street, Grimsby | Results |
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