| 09 May 1998 | First Round | Broughton Second XI v Brigg Town Second XI | Recreation Ground, Broughton | Results |
| 31 May 1998 | Second Round | Keelby Second XI v Broughton Second XI | Village Green, Keelby | Results |
| 09 May 1998 | Group A | Keelby Second XI v Littlefields Second XI | Keelby Sports Ground, Keelby | Results |
| 30 Apr 1998 | Group A | Grimsby Town Second XI v Broughton Second XI | Augusta Street, Grimsby | Results |
| 10 May 1998 | Group A | Littlefields Second XI v Brigg Town Second XI | Drewery Brothers Ground, Grimsby | Results |
| 30 May 1998 | Group A | Grimsby Town Second XI v Keelby Second XI | Augusta Street, Grimsby | Results |
| 30 Apr 1998 | Group A | Broughton Second XI v Littlefields Second XI | Recreation Ground, Broughton | Results |
| 31 May 1998 | Group A | Brigg Town Second XI v Grimsby Town Second XI | Brigg Recreation Ground, Brigg | Results |
| 28 Jun 1998 | Group A | Brigg Town Second XI v Keelby Second XI | Brigg Recreation Ground, Brigg | Results |
| 28 Jun 1998 | Group A | Littlefields Second XI v Grimsby Town Second XI | Drewery Brothers Ground, Grimsby | Results |
| 09 May 1998 | Group B | Cherry Willingham Second XI v Hartsholme Second XI | Playing Fields, Cherry Willingham | Results |
| 10 May 1998 | Group B | Nettleham Second XI v Hykeham Second XI | Mulsanne Park, Nettleham | Results |
| 30 May 1998 | Group B | Nettleham Second XI v Cherry Willingham Second XI | Mulsanne Park, Nettleham | Results |
| 30 May 1998 | Group B | Hykeham Second XI v Hartsholme Second XI | Memorial Field, North Hykeham | Results |
| 31 May 1998 | Group B | Cherry Willingham Second XI v Hykeham Second XI | Playing Fields, Cherry Willingham | Results |
| 28 Jun 1998 | Group B | Hartsholme Second XI v Nettleham Second XI | Ashby Avenue, Hartsholme | Results |
| 09 May 1998 | Group C | Louth Second XI v Alford Second XI | London Road, Louth | Results |
| 09 May 1998 | Group C | Market Rasen Second XI v Caistor Town Second XI | Rase Park, Market Rasen | Results |
| 10 May 1998 | Group C | Bottesford Town Second XI v Market Rasen Second XI | Birch Park, Bottesford | Results |
| 10 May 1998 | Group C | Alford Second XI v Caistor Town Second XI | Train Fen Holt, Alford | Results |
| 30 May 1998 | Group C | Bottesford Town Second XI v Louth Second XI | Birch Park, Bottesford | Results |
| 30 May 1998 | Group C | Market Rasen Second XI v Alford Second XI | Rase Park, Market Rasen | Results |
| 31 May 1998 | Group C | Louth Second XI v Market Rasen Second XI | London Road, Louth | Results |
| 31 May 1998 | Group C | Caistor Town Second XI v Bottesford Town Second XI | Brigg Road Ground, Caistor | Results |
| 28 Jun 1998 | Group C | Caistor Town Second XI v Louth Second XI | Brigg Road Ground, Caistor | Results |
| 28 Jun 1998 | Group C | Alford Second XI v Bottesford Second XI | Train Fen Holt, Alford | Results |
| 09 May 1998 | Group D | Alkborough Second XI v Normanby Park Second XI | West Halton Lane, Alkborough | Results |
| 09 May 1998 | Group D | Messingham Second XI v Normanby Park Works Second XI | Memorial Playing Field, Messingham | Results |
| 09 May 1998 | Group D | Outcasts Second XI v Scunthorpe Town Second XI | Hirst Priory Park, Crowle | Results |
| 10 May 1998 | Group D | Normanby Park Second XI v Scunthorpe Town Second XI | Normanby Park Estate, Scunthorpe | Results |
| 10 May 1998 | Group D | Alkborough Second XI v Messingham Second XI | West Halton Lane, Alkborough | Results |
| 10 May 1998 | Group D | Normanby Park Works Second XI v Outcasts Second XI | Cemetery Road Sports Ground, Brumby | Results |
| 30 May 1998 | Group D | Scunthorpe Town Second XI v Normanby Park Works Second XI | Heslam Park, Scunthorpe | Results |
| 30 May 1998 | Group D | Messingham Second XI v Normanby Park Second XI | Memorial Playing Field, Messingham | Results |
| 30 May 1998 | Group D | Outcasts Second XI v Alkborough Second XI | Hirst Priory Park, Crowle | Results |
| 31 May 1998 | Group D | Scunthorpe Town Second XI v Alkborough Second XI | Heslam Park, Scunthorpe | Results |
| 31 May 1998 | Group D | Normanby Park Second XI v Normanby Park Works Second XI | Normanby Park Estate, Scunthorpe | Results |
| 31 May 1998 | Group D | Messingham Second XI v Outcasts Second XI | Memorial Playing Field, Messingham | Results |
| 28 Jun 1998 | Group D | Scunthorpe Town Second XI v Messingham Second XI | Heslam Park, Scunthorpe | Results |
| 28 Jun 1998 | Group D | Normanby Park Works Second XI v Alkborough Second XI | Cemetery Road Sports Ground, Brumby | Results |
| 28 Jun 1998 | Group D | Normanby Park Second XI v Outcasts Second XI | Normanby Park Estate, Scunthorpe | Results |
| 19 Jul 1998 | Semi-Final | Grimsby Town Second XI v Messingham Second XI | Augusta Street, Grimsby | Results |
| 30 Jun 1998 | Semi-Final | Nettleham Second XI v Market Rasen Second XI | Mulsanne Park, Nettleham | Results |
| 09 Aug 1998 | Final | Messingham Second XI v Nettleham Second XI | Memorial Playing Field, Messingham | Results |
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