| 25 Apr 1999 | | Barton Town Third XI v Brigg Town Third XI | Marsh Lane, Barton on Humber | Results |
| 30 Jun 1999 | | Haxey Third XI v Kirton Lindsey Second XI | Haxey Lane, Haxey | Results |
| 25 Apr 1999 | | Lea Park v Hibaldstow Second XI | Lea Park, Lea | Results |
| 02 May 1999 | | Brigg Town Third XI v Caistor Town Fourth XI | Brigg Recreation Ground, Brigg | Results |
| 02 May 1999 | | Hibaldstow Second XI v Haxey Third XI | Station Road, Hibaldstow | Results |
| 30 May 1999 | | Kirton Lindsey Second XI v Barton Town Third XI | Redbourne Mere, Kirton in Lindsey | Results |
| 16 May 1999 | | Barton Town Third XI v Caistor Town Fourth XI | Marsh Lane, Barton on Humber | Results |
| 16 May 1999 | | Hibaldstow Second XI v Brigg Town Third XI | Station Road, Hibaldstow | Results |
| 16 May 1999 | | Lea Park v Kirton Lindsey Second XI | Lea Park, Lea | Results |
| 23 May 1999 | | Caistor Town Fourth XI v Lea Park | Brigg Road Ground, Caistor | Results |
| 23 May 1999 | | Haxey Third XI v Barton Town Third XI | Haxey Lane, Haxey | Results |
| 23 May 1999 | | Kirton Lindsey Second XI v Brigg Town Third XI | Redbourne Mere, Kirton in Lindsey | Results |
| 05 Sep 1999 | | Barton Town Third XI v Hibaldstow Second XI | Marsh Lane, Barton on Humber | Results |
| 06 Jun 1999 | | Kirton Lindsey Second XI v Caistor Town Fourth XI | Redbourne Mere, Kirton in Lindsey | Results |
| 06 Jun 1999 | | Lea Park v Haxey Third XI | Lea Park, Lea | Results |
| 13 Jun 1999 | | Brigg Town Third XI v Lea Park | Brigg Recreation Ground, Brigg | Results |
| 05 Sep 1999 | | Haxey Third XI v Caistor Town Fourth XI | Haxey Lane, Haxey | Results |
| 13 Jun 1999 | | Hibaldstow Second XI v Kirton Lindsey Second XI | Station Road, Hibaldstow | Results |
| 11 Jul 1999 | | Haxey Third XI v Brigg Town Third XI | Haxey Lane, Haxey | Results |
| 11 Jul 1999 | | Hibaldstow Second XI v Caistor Town Fourth XI | Station Road, Hibaldstow | Results |
| 11 Jul 1999 | | Lea Park v Barton Town Third XI | Lea Park, Lea | Results |
| 18 Jul 1999 | | Brigg Town Third XI v Hibaldstow Second XI | Brigg Recreation Ground, Brigg | Results |
| 18 Jul 1999 | | Caistor Town Fourth XI v Barton Town Third XI | Brigg Road Ground, Caistor | Results |
| 18 Jul 1999 | | Kirton Lindsey Second XI v Lea Park | Redbourne Mere, Kirton in Lindsey | Results |
| 01 Aug 1999 | | Barton Town Third XI v Kirton Lindsey Second XI | Marsh Lane, Barton on Humber | Results |
| 01 Aug 1999 | | Caistor Town Fourth XI v Brigg Town Third XI | Brigg Road Ground, Caistor | Results |
| 01 Aug 1999 | | Haxey Third XI v Hibaldstow Second XI | Haxey Lane, Haxey | Results |
| 15 Aug 1999 | | Barton Town Third XI v Haxey Third XI | Marsh Lane, Barton on Humber | Results |
| 08 Aug 1999 | | Brigg Town Third XI v Kirton Lindsey Second XI | Brigg Recreation Ground, Brigg | Results |
| 08 Aug 1999 | | Lea Park v Caistor Town Fourth XI | Lea Park, Lea | Results |
| 22 Aug 1999 | | Brigg Town Third XI v Barton Town Third XI | Brigg Recreation Ground, Brigg | Results |
| 22 Aug 1999 | | Hibaldstow Second XI v Lea Park | Station Road, Hibaldstow | Results |
| 22 Aug 1999 | | Kirton Lindsey Second XI v Haxey Third XI | Redbourne Mere, Kirton in Lindsey | Results |
| 29 Aug 1999 | | Caistor Town Fourth XI v Kirton Lindsey Second XI | Brigg Road Ground, Caistor | Results |
| 29 Aug 1999 | | Haxey Third XI v Lea Park | Haxey Lane, Haxey | Results |
| 29 Aug 1999 | | Hibaldstow Second XI v Barton Town Third XI | Station Road, Hibaldstow | Results |
| 12 Sep 1999 | | Caistor Town Fourth XI v Haxey Third XI | Brigg Road Ground, Caistor | Results |
| 12 Sep 1999 | | Kirton Lindsey Second XI v Hibaldstow Second XI | Redbourne Mere, Kirton in Lindsey | Results |
| 12 Sep 1999 | | Lea Park v Brigg Town Third XI | Lea Park, Lea | Results |
| 19 Sep 1999 | | Barton Town Third XI v Lea Park | Marsh Lane, Barton on Humber | Results |
| 19 Sep 1999 | | Brigg Town Third XI v Haxey Third XI | Brigg Recreation Ground, Brigg | Results |
| 19 Sep 1999 | | Caistor Town Fourth XI v Hibaldstow Second XI | Brigg Road Ground, Caistor | Results |
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