| 07 May 1990 | | Broughton Second XI v Scunthorpe Town Third XI | Recreation Ground, Broughton | Results |
| 30 Apr 1990 | First Round | Alkborough Second XI v Smith-Corona Marchant | West Halton Lane, Alkborough | Results |
| 30 Apr 1990 | First Round | Broughton Second XI v Scunthorpe Town Third XI | Recreation Ground, Broughton | Results |
| 30 Apr 1990 | First Round | Dee Jays v Findus | Ashby Ville Sports Ground, Scunthorpe | Results |
| 30 Apr 1990 | First Round | East Halton v Norsk Hydro | Townside Farm, East Halton | Results |
| 30 Apr 1990 | First Round | Findus Second XI v Brigg Town Second XI | Hewitts Circus, Humberstone | Results |
| 31 May 1990 | Second Round | Keelby v Alkborough Second XI | Keelby Sports Ground, Keelby | Results |
| 31 May 1990 | Second Round | Bottesford Town v Belton Second XI | Birch Park, Bottesford | Results |
| 31 May 1990 | Second Round | Normanby Park Works Third XI v not known | Cemetery Road Sports Ground, Brumby | Results |
| 31 May 1990 | Second Round | Keelby Second XI v South Kelsey Second XI | Keelby Sports Ground, Keelby | Results |
| 31 May 1990 | Second Round | Scunthorpe Town Third XI v Epworth | Co-operative Sports Ground, Scunthorpe | Results |
| 31 May 1990 | Second Round | Dee Jays v John Margrave | Ashby Ville Sports Ground, Scunthorpe | Results |
| 31 May 1990 | Second Round | East Halton v Brigg Town Second XI | Townside Farm, East Halton | Results |
| 31 May 1990 | Second Round | Kirton Lindsey Second XI v Hibaldstow | Redbourne Mere, Kirton in Lindsey | Results |
| 30 Jun 1990 | Quarter-Final | Alkborough Second XI v Bottesford Town | West Halton Lane, Alkborough | Results |
| 30 Jun 1990 | Quarter-Final | Normanby Park Works Third XI v Keelby Second XI | Cemetery Road Sports Ground, Brumby | Results |
| 30 Jun 1990 | Quarter-Final | Scunthorpe Town Third XI v Dee Jays | Co-operative Sports Ground, Scunthorpe | Results |
| 30 Jun 1990 | Quarter-Final | East Halton v Hibaldstow | Townside Farm, East Halton | Results |
| 31 Jul 1990 | Semi-Final | Alkborough Second XI v Keelby Second XI | West Halton Lane, Alkborough | Results |
| 31 Jul 1990 | Semi-Final | Dee Jays v Hibaldstow | Ashby Ville Sports Ground, Scunthorpe | Results |
| 31 Jul 1990 | Final | Dee Jays v Keelby Second XI | Recreation Ground, Broughton | Results |
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