| 20 May 1990 | First Round | Broughton v Cleethorpes | Recreation Ground, Broughton | Results |
| 01 Aug 1990 | Semi-Final | Cleethorpes v Appleby Frodingham | Sports Ground, Cleethorpes | Results |
| 30 Apr 1990 | Preliminary Round | Brigg Town v Outcasts | Brigg Recreation Ground, Brigg | Results |
| 13 May 1990 | Preliminary Round | Southcliffe St Andrews v Bracebridge Heath | Sobraon Barracks, Lincoln | Results |
| 03 Jun 1990 | First Round | Alford v Market Rasen | Train Fen Holt, Alford | Results |
| 03 Jun 1990 | First Round | Ruston Marconi Sports Club v Nettleham | Ruston-Bucyrus Ground, Lincoln | Results |
| 03 Jun 1990 | First Round | Skegness v Louth | Richmond Drive, Skegness | Results |
| 03 Jun 1990 | First Round | Scunthorpe Town v Ross Sports | Heslam Park, Scunthorpe | Results |
| 03 Jun 1990 | First Round | Barton Town v Haxey | Marsh Lane, Barton on Humber | Results |
| 03 Jun 1990 | First Round | Nettleton Mines v Caistor Town | Lysaghts Sports Ground, Holton le Moor | Results |
| 03 Jun 1990 | First Round | Holton-le-Clay v Belton | Tetney Lane, Holton-le-Clay | Results |
| 03 Jun 1990 | First Round | Grimsby Town v Brigg Town | Augusta Street, Grimsby | Results |
| 03 Jun 1990 | First Round | Kirton Lindsey v Hykeham | Redbourne Mere, Kirton in Lindsey | Results |
| 03 Jun 1990 | First Round | Lincoln Claytons v Grimsby British Rail Sports Association | Clayton's Sports Club Ground, Lincoln | Results |
| 03 Jun 1990 | First Round | Alkborough v Normanby Park Works | West Halton Lane, Alkborough | Results |
| 03 Jun 1990 | First Round | Saxilby v Hartsholme | Saxilby Sports Association Ground, Saxilby | Results |
| 03 Jun 1990 | First Round | Normanby Park v Messingham | Normanby Park Estate, Scunthorpe | Results |
| 03 Jun 1990 | First Round | South Kelsey v Appleby Frodingham | Waddingham Road, South Kelsey | Results |
| 03 Jun 1990 | First Round | not known v Nuform Sports | not known | Results |
| 24 Jun 1990 | Second Round | not known v not known | not known | Results |
| 24 Jun 1990 | Second Round | not known v Appleby Frodingham | not known | Results |
| 24 Jun 1990 | Second Round | not known v Lincoln Claytons | not known | Results |
| 24 Jun 1990 | Second Round | Cleethorpes Third XI v Nettleton Mines | Sports Ground, Cleethorpes | Results |
| 24 Jun 1990 | Second Round | Messingham v Saxilby | Memorial Playing Field, Messingham | Results |
| 24 Jun 1990 | Second Round | Normanby Park Works v Grimsby Town | Cemetery Road Sports Ground, Brumby | Results |
| 24 Jun 1990 | Second Round | not known v not known | not known | Results |
| 24 Jun 1990 | Second Round | not known v not known | not known | Results |
| 15 Jul 1990 | Quarter-Final | not known v Lincoln Claytons | not known | Results |
| 15 Jul 1990 | Quarter-Final | Normanby Park Works v Messingham | Cemetery Road Sports Ground, Brumby | Results |
| 30 Jun 1990 | Quarter-Final | not known v Appleby Frodingham | not known | Results |
| 30 Jun 1990 | Quarter-Final | not known v Cleethorpes Third XI | not known | Results |
| 05 Aug 1990 | Semi-Final | Lincoln Claytons v Messingham | Clayton's Sports Club Ground, Lincoln | Results |
| 16 Sep 1990 | Final | Lincoln Claytons v Appleby Frodingham | Brumby Hall, Scunthorpe | Results |
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