| 25 Apr 1999 | | Blyton v Haxey Fourth XI | Sandbeck Lane, Blyton | Results |
| 25 Apr 1999 | | Bottesford Town Third XI v Hygena Packaging | Birch Park, Bottesford | Results |
| 25 Apr 1999 | | Roses v Barton Town Fourth XI | Rose Brothers Sports Ground, Gainsborough | Results |
| 13 Jun 1999 | | Scotter v Epworth | Scotter | Results |
| 02 May 1999 | | Barton Town Fourth XI v Epworth | Marsh Lane, Barton on Humber | Results |
| 02 May 1999 | | Blyton v Roses | Sandbeck Lane, Blyton | Results |
| 02 May 1999 | | Haxey Fourth XI v Bottesford Town Third XI | Haxey Lane, Haxey | Results |
| 02 May 1999 | | Hygena Packaging v Scotter | Co-operative Sports Ground, Scunthorpe | Results |
| 16 May 1999 | | Bottesford Town Third XI v Roses | Birch Park, Bottesford | Results |
| 16 May 1999 | | Epworth v Blyton | Carrside, Epworth | Results |
| 16 May 1999 | | Haxey Fourth XI v Scotter | Haxey Lane, Haxey | Results |
| 16 May 1999 | | Hygena Packaging v Barton Town Fourth XI | Co-operative Sports Ground, Scunthorpe | Results |
| 23 May 1999 | | Barton Town Fourth XI v Haxey Fourth XI | Marsh Lane, Barton on Humber | Results |
| 23 May 1999 | | Blyton v Hygena Packaging | Sandbeck Lane, Blyton | Results |
| 23 May 1999 | | Epworth v Bottesford Town Third XI | Carrside, Epworth | Results |
| 23 May 1999 | | Scotter v Roses | Scotter | Results |
| 20 Jun 1999 | | Blyton v Barton Town Fourth XI | Sandbeck Lane, Blyton | Results |
| 20 Jun 1999 | | Epworth v Hygena Packaging | Carrside, Epworth | Results |
| 20 Jun 1999 | | Haxey Fourth XI v Roses | Haxey Lane, Haxey | Results |
| 20 Jun 1999 | | Scotter v Bottesford Town Third XI | Scotter | Results |
| 27 Jun 1999 | | Barton Town Fourth XI v Scotter | Marsh Lane, Barton on Humber | Results |
| 27 Jun 1999 | | Bottesford Town Third XI v Blyton | Birch Park, Bottesford | Results |
| 27 Jun 1999 | | Hygena Packaging v Haxey Fourth XI | Co-operative Sports Ground, Scunthorpe | Results |
| 27 Jun 1999 | | Roses v Epworth | Rose Brothers Sports Ground, Gainsborough | Results |
| 11 Jul 1999 | | Barton Town Fourth XI v Bottesford Town Third XI | Marsh Lane, Barton on Humber | Results |
| 22 Aug 1999 | | Epworth v Haxey Fourth XI | Carrside, Epworth | Results |
| 11 Jul 1999 | | Hygena Packaging v Roses | Co-operative Sports Ground, Scunthorpe | Results |
| 11 Jul 1999 | | Scotter v Blyton | Scotter | Results |
| 18 Jul 1999 | | Barton Town Fourth XI v Hygena Packaging | Marsh Lane, Barton on Humber | Results |
| 18 Jul 1999 | | Blyton v Epworth | Sandbeck Lane, Blyton | Results |
| 18 Jul 1999 | | Roses v Bottesford Town Third XI | Rose Brothers Sports Ground, Gainsborough | Results |
| 25 Jul 1999 | | Barton Town Fourth XI v Roses | Marsh Lane, Barton on Humber | Results |
| 25 Jul 1999 | | Epworth v Scotter | Carrside, Epworth | Results |
| 25 Jul 1999 | | Haxey Fourth XI v Blyton | Haxey Lane, Haxey | Results |
| 25 Jul 1999 | | Hygena Packaging v Bottesford Town Third XI | Co-operative Sports Ground, Scunthorpe | Results |
| 01 Aug 1999 | | Bottesford Town Third XI v Haxey Fourth XI | Birch Park, Bottesford | Results |
| 01 Aug 1999 | | Epworth v Barton Town Fourth XI | Carrside, Epworth | Results |
| 01 Aug 1999 | | Roses v Blyton | Rose Brothers Sports Ground, Gainsborough | Results |
| 01 Aug 1999 | | Scotter v Hygena Packaging | Scotter | Results |
| 08 Aug 1999 | | Bottesford Town Third XI v Epworth | Birch Park, Bottesford | Results |
| 08 Aug 1999 | | Haxey Fourth XI v Barton Town Fourth XI | Haxey Lane, Haxey | Results |
| 08 Aug 1999 | | Hygena Packaging v Blyton | Co-operative Sports Ground, Scunthorpe | Results |
| 08 Aug 1999 | | Roses v Scotter | Rose Brothers Sports Ground, Gainsborough | Results |
| 29 Aug 1999 | | Barton Town Fourth XI v Blyton | Marsh Lane, Barton on Humber | Results |
| 29 Aug 1999 | | Bottesford Town Third XI v Scotter | Birch Park, Bottesford | Results |
| 29 Aug 1999 | | Hygena Packaging v Epworth | Co-operative Sports Ground, Scunthorpe | Results |
| 29 Aug 1999 | | Roses v Haxey Fourth XI | Rose Brothers Sports Ground, Gainsborough | Results |
| 05 Sep 1999 | | Scotter v Haxey Fourth XI | Scotter | Results |
| 12 Sep 1999 | | Blyton v Bottesford Town Third XI | Sandbeck Lane, Blyton | Results |
| 12 Sep 1999 | | Epworth v Roses | Carrside, Epworth | Results |
| 12 Sep 1999 | | Haxey Fourth XI v Hygena Packaging | Haxey Lane, Haxey | Results |
| 12 Sep 1999 | | Scotter v Barton Town Fourth XI | Scotter | Results |
| 19 Sep 1999 | | Blyton v Scotter | Sandbeck Lane, Blyton | Results |
| 19 Sep 1999 | | Bottesford Town Third XI v Barton Town Fourth XI | Birch Park, Bottesford | Results |
| 19 Sep 1999 | | Haxey Fourth XI v Epworth | Haxey Lane, Haxey | Results |
| 19 Sep 1999 | | Roses v Hygena Packaging | Rose Brothers Sports Ground, Gainsborough | Results |
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