| 18 Apr 1998 | Preliminary Round | Grimsby Town v Bracebridge Heath Second XI | Augusta Street, Grimsby | Results |
| 09 May 1998 | First Round | Alford v Alkborough | Train Fen Holt, Alford | Results |
| 09 May 1998 | First Round | Barton Town Second XI v Market Rasen | Marsh Lane, Barton on Humber | Results |
| 09 May 1998 | First Round | Bottesford Town v Rustons | Birch Park, Bottesford | Results |
| 09 May 1998 | First Round | Brigg Town v Louth | Brigg Recreation Ground, Brigg | Results |
| 09 May 1998 | First Round | Cleethorpes Third XI v Outcasts | Sports Ground, Cleethorpes | Results |
| 09 May 1998 | First Round | Caistor Town v Messingham | Brigg Road Ground, Caistor | Results |
| 09 May 1998 | First Round | Grimsby Town v Immingham Blossom Way | Augusta Street, Grimsby | Results |
| 09 May 1998 | First Round | Hartsholme v Skegness | Ashby Avenue, Hartsholme | Results |
| 09 May 1998 | First Round | Holton-le-Clay v Haxey | Tetney Lane, Holton-le-Clay | Results |
| 09 May 1998 | First Round | Millennium Chemicals v Keelby | Clee Road, Grimsby | Results |
| 09 May 1998 | First Round | Nettleton Mines v Cherry Willingham | Lysaghts Sports Ground, Holton le Moor | Results |
| 09 May 1998 | First Round | Normanby Park v Littlefields | Normanby Park Estate, Scunthorpe | Results |
| 09 May 1998 | First Round | Normanby Park Works v Nettleham | Cemetery Road Sports Ground, Brumby | Results |
| 09 May 1998 | First Round | Owmby v Broughton | Todmoor, Owmby by Spital | Results |
| 09 May 1998 | First Round | Scunthorpe Town v Hykeham | Heslam Park, Scunthorpe | Results |
| 09 May 1998 | First Round | South Kelsey v Horncastle | Waddingham Road, South Kelsey | Results |
| 30 May 1998 | Second Round | Alkborough v Normanby Park Works | West Halton Lane, Alkborough | Results |
| 30 May 1998 | Second Round | Louth v Scunthorpe Town | London Road, Louth | Results |
| 30 May 1998 | Second Round | Messingham v Littlefields | Memorial Playing Field, Messingham | Results |
| 30 May 1998 | Second Round | Grimsby Town v Outcasts | Augusta Street, Grimsby | Results |
| 30 May 1998 | Second Round | Skegness v Horncastle | Richmond Drive, Skegness | Results |
| 30 May 1998 | Second Round | Millennium Chemicals v Bottesford Town | Clee Road, Grimsby | Results |
| 30 May 1998 | Second Round | Nettleton Mines v Haxey | Lysaghts Sports Ground, Holton le Moor | Results |
| 30 May 1998 | Second Round | Owmby v Market Rasen | Todmoor, Owmby by Spital | Results |
| 28 Jun 1998 | Quarter-Final | Normanby Park Works v Louth | Cemetery Road Sports Ground, Brumby | Results |
| 28 Jun 1998 | Quarter-Final | Messingham v Grimsby Town | Memorial Playing Field, Messingham | Results |
| 28 Jun 1998 | Quarter-Final | Skegness v Millennium Chemicals | Richmond Drive, Skegness | Results |
| 28 Jun 1998 | Quarter-Final | Haxey v Owmby | Haxey Lane, Haxey | Results |
| 19 Jul 1998 | Semi-Final | Normanby Park Works v Skegness | Cemetery Road Sports Ground, Brumby | Results |
| 19 Jul 1998 | Semi-Final | Grimsby Town v Haxey | Augusta Street, Grimsby | Results |
| 16 Aug 1998 | Final | Grimsby Town v Skegness | Augusta Street, Grimsby | Results |
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