| 07 May 1989 | Preliminary Round | Scunthorpe Town v Nettleham | Heslam Park, Scunthorpe | Results |
| 07 May 1989 | Preliminary Round | Haxey v Holton-le-Clay | Haxey Lane, Haxey | Results |
| 28 May 1989 | First Round | Nettleton Mines v Hartsholme | Lysaghts Sports Ground, Holton le Moor | Results |
| 30 Apr 1989 | First Round | Outcasts v Market Rasen | Hirst Priory Park, Crowle | Results |
| 28 May 1989 | First Round | Lincoln Claytons v Broughton | Clayton's Sports Club Ground, Lincoln | Results |
| 28 May 1989 | First Round | Grimsby British Rail Sports Association v Alkborough | Carr Lane, Grimsby | Results |
| 28 May 1989 | First Round | Scunthorpe Town v Saxilby | Heslam Park, Scunthorpe | Results |
| 28 May 1989 | First Round | St John's Hospital v Haxey | St John's Hospital, Bracebridge Heath | Results |
| 28 May 1989 | First Round | Cleethorpes Third XI v Louth | Sports Ground, Cleethorpes | Results |
| 28 May 1989 | First Round | Caistor Town v Messingham | Brigg Road Ground, Caistor | Results |
| 28 May 1989 | First Round | South Kelsey v Barton Town | Waddingham Road, South Kelsey | Results |
| 28 May 1989 | First Round | Grimsby Town v Nuform Sports | Augusta Street, Grimsby | Results |
| 28 May 1989 | First Round | Skegness v Hykeham | Richmond Drive, Skegness | Results |
| 28 May 1989 | First Round | Normanby Park Works v Southcliffe St Andrews | Cemetery Road Sports Ground, Brumby | Results |
| 28 May 1989 | First Round | Appleby Frodingham v Belton | Brumby Hall, Scunthorpe | Results |
| 28 May 1989 | First Round | Ross Sports v Brigg Town | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 28 May 1989 | First Round | Alford v Normanby Park | Train Fen Holt, Alford | Results |
| 28 May 1989 | First Round | Kirton Lindsey v Rustons | Redbourne Mere, Kirton in Lindsey | Results |
| 18 Jun 1989 | Second Round | Normanby Park Works v Messingham | Cemetery Road Sports Ground, Brumby | Results |
| 18 Jun 1989 | Second Round | Cleethorpes Third XI v not known | Sports Ground, Cleethorpes | Results |
| 18 Jun 1989 | Second Round | not known v Ross Sports | not known | Results |
| 18 Jun 1989 | Second Round | Market Rasen v not known | Rase Park, Market Rasen | Results |
| 18 Jun 1989 | Second Round | not known v not known | not known | Results |
| 31 May 1989 | Second Round | not known v Lincoln Claytons | not known | Results |
| 18 Jun 1989 | Second Round | not known v not known | not known | Results |
| 18 Jun 1989 | Second Round | not known v not known | not known | Results |
| 30 Jun 1989 | Quarter-Final | Ross Sports v Cleethorpes Third XI | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 09 Jul 1989 | Quarter-Final | Lincoln Claytons v not known | Clayton's Sports Club Ground, Lincoln | Results |
| 09 Jul 1989 | Quarter-Final | Market Rasen v Messingham | Rase Park, Market Rasen | Results |
| 09 Jul 1989 | Quarter-Final | not known v not known | not known | Results |
| 30 Jun 1989 | Semi-Final | Cleethorpes Third XI v Messingham | Sports Ground, Cleethorpes | Results |
| 30 Jul 1989 | Semi-Final | not known v Lincoln Claytons | not known | Results |
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