| 18 May 1986 | First Round | Broughton v Grimsby Town | Recreation Ground, Broughton | Results |
| 11 May 1986 | Preliminary Round | Nettleton Mines v Caistor Town | Lysaghts Sports Ground, Holton le Moor | Results |
| 11 May 1986 | Preliminary Round | Barton Town v Hykeham | Marsh Lane, Barton on Humber | Results |
| 01 Jun 1986 | First Round | Rustons v Alford | Newark Road, Lincoln | Results |
| 01 Jun 1986 | First Round | Normanby Park Works v Alkborough | Cemetery Road Sports Ground, Brumby | Results |
| 01 Jun 1986 | First Round | Normanby Park v South Kelsey | Normanby Park Estate, Scunthorpe | Results |
| 01 Jun 1986 | First Round | Ruston Bucyrus v Saxilby | Ruston-Bucyrus Ground, Lincoln | Results |
| 01 Jun 1986 | First Round | Nuform Sports v not known | Nuform Ground, Scunthorpe | Results |
| 31 May 1986 | First Round | Market Rasen v Cleethorpes Third XI | Rase Park, Market Rasen | Results |
| 01 Jun 1986 | First Round | Scunthorpe Town v Messingham | Heslam Park, Scunthorpe | Results |
| 01 Jun 1986 | First Round | St John's Hospital v Hartsholme | St John's Hospital, Bracebridge Heath | Results |
| 04 May 1986 | First Round | Ross Sports v Outcasts | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 01 Jun 1986 | First Round | Broughton v Grimsby Town | Recreation Ground, Broughton | Results |
| 01 Jun 1986 | First Round | not known v Louth | not known | Results |
| 01 Jun 1986 | First Round | Appleby Frodingham v Grimsby British Rail Sports Association | Brumby Hall, Scunthorpe | Results |
| 01 Jun 1986 | First Round | Nettleham v Skegness | Mulsanne Park, Nettleham | Results |
| 31 May 1986 | First Round | Lincoln Claytons v Belton | Clayton's Sports Club Ground, Lincoln | Results |
| 01 Jun 1986 | First Round | Holton-le-Clay v Haxey | Tetney Lane, Holton-le-Clay | Results |
| 01 Jun 1986 | First Round | East Halton v Southcliffe St Andrews | Townside Farm, East Halton | Results |
| 29 Jun 1986 | Second Round | Nuform Sports v Grimsby Town | Nuform Ground, Scunthorpe | Results |
| 29 Jun 1986 | Second Round | Appleby Frodingham v not known | Brumby Hall, Scunthorpe | Results |
| 29 Jun 1986 | Second Round | not known v Lincoln Claytons | not known | Results |
| 29 Jun 1986 | Second Round | not known v not known | not known | Results |
| 29 Jun 1986 | Second Round | Messingham v Ross Sports | Memorial Playing Field, Messingham | Results |
| 29 Jun 1986 | Second Round | not known v not known | not known | Results |
| 29 Jun 1986 | Second Round | Saxilby v not known | Saxilby Sports Association Ground, Saxilby | Results |
| 29 Jun 1986 | Second Round | not known v not known | not known | Results |
| 30 Jun 1986 | Quarter-Final | Appleby Frodingham v Messingham | Brumby Hall, Scunthorpe | Results |
| 27 Jul 1986 | Quarter-Final | Saxilby v not known | Saxilby Sports Association Ground, Saxilby | Results |
| 27 Jul 1986 | Quarter-Final | not known v not known | not known | Results |
| 27 Jul 1986 | Quarter-Final | not known v not known | not known | Results |
| 10 Aug 1986 | Semi-Final | Appleby Frodingham v not known | Brumby Hall, Scunthorpe | Results |
| 10 Aug 1986 | Semi-Final | Saxilby v not known | Saxilby Sports Association Ground, Saxilby | Results |
| 17 Aug 1986 | Final | Appleby Frodingham v Saxilby | Augusta Street, Grimsby | Results |
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