| 25 Apr 1999 | | Appleby Frodingham Third XI v Laughton | Brumby Hall, Scunthorpe | Results |
| 01 Aug 1999 | | Beckingham v Burton Stather | Southfield Lane, Beckingham | Results |
| 02 May 1999 | | Beckingham v Gunness | Southfield Lane, Beckingham | Results |
| 02 May 1999 | | Corringham v Burton Stather | Rose Brothers Sports Ground, Gainsborough | Results |
| 02 May 1999 | | Scunthorpe Town Fourth XI v Appleby Frodingham Third XI | Co-operative Sports Ground, Scunthorpe | Results |
| 16 May 1999 | | Burton Stather v Appleby Frodingham Third XI | Burton Stather Cricket Ground, Burton Stather | Results |
| 16 May 1999 | | Corringham v Laughton | Rose Brothers Sports Ground, Gainsborough | Results |
| 16 May 1999 | | Gunness v Scunthorpe Town Fourth XI | Gunness | Results |
| 23 May 1999 | | Beckingham v Scunthorpe Town Fourth XI | Southfield Lane, Beckingham | Results |
| 06 Jun 1999 | | Beckingham v Corringham | Southfield Lane, Beckingham | Results |
| 06 Jun 1999 | | Burton Stather v Scunthorpe Town Fourth XI | Burton Stather Cricket Ground, Burton Stather | Results |
| 06 Jun 1999 | | Laughton v Gunness | Laughton Cricket Ground, Laughton | Results |
| 13 Jun 1999 | | Burton Stather v Gunness | Burton Stather Cricket Ground, Burton Stather | Results |
| 13 Jun 1999 | | Corringham v Appleby Frodingham Third XI | Rose Brothers Sports Ground, Gainsborough | Results |
| 13 Jun 1999 | | Laughton v Beckingham | Laughton Cricket Ground, Laughton | Results |
| 20 Jun 1999 | | Beckingham v Appleby Frodingham Third XI | Southfield Lane, Beckingham | Results |
| 20 Jun 1999 | | Gunness v Corringham | Gunness | Results |
| 20 Jun 1999 | | Scunthorpe Town Fourth XI v Laughton | Co-operative Sports Ground, Scunthorpe | Results |
| 27 Jun 1999 | | Gunness v Appleby Frodingham Third XI | Gunness | Results |
| 27 Jun 1999 | | Laughton v Burton Stather | Laughton Cricket Ground, Laughton | Results |
| 27 Jun 1999 | | Scunthorpe Town Fourth XI v Beckingham | Co-operative Sports Ground, Scunthorpe | Results |
| 18 Jul 1999 | | Appleby Frodingham Third XI v Scunthorpe Town Fourth XI | Brumby Hall, Scunthorpe | Results |
| 18 Jul 1999 | | Burton Stather v Corringham | Burton Stather Cricket Ground, Burton Stather | Results |
| 18 Jul 1999 | | Gunness v Beckingham | Gunness | Results |
| 25 Jul 1999 | | Burton Stather v Beckingham | Burton Stather Cricket Ground, Burton Stather | Results |
| 25 Jul 1999 | | Corringham v Scunthorpe Town Fourth XI | Rose Brothers Sports Ground, Gainsborough | Results |
| 25 Jul 1999 | | Laughton v Appleby Frodingham Third XI | Laughton Cricket Ground, Laughton | Results |
| 08 Aug 1999 | | Appleby Frodingham Third XI v Burton Stather | Brumby Hall, Scunthorpe | Results |
| 08 Aug 1999 | | Laughton v Corringham | Laughton Cricket Ground, Laughton | Results |
| 08 Aug 1999 | | Scunthorpe Town Fourth XI v Gunness | Co-operative Sports Ground, Scunthorpe | Results |
| 22 Aug 1999 | | Corringham v Beckingham | Rose Brothers Sports Ground, Gainsborough | Results |
| 22 Aug 1999 | | Gunness v Laughton | Gunness | Results |
| 22 Aug 1999 | | Scunthorpe Town Fourth XI v Burton Stather | Co-operative Sports Ground, Scunthorpe | Results |
| 05 Sep 1999 | | Appleby Frodingham Third XI v Corringham | Brumby Hall, Scunthorpe | Results |
| 29 Aug 1999 | | Beckingham v Laughton | Southfield Lane, Beckingham | Results |
| 29 Aug 1999 | | Gunness v Burton Stather | Gunness | Results |
| 12 Sep 1999 | | Appleby Frodingham Third XI v Beckingham | Brumby Hall, Scunthorpe | Results |
| 12 Sep 1999 | | Corringham v Gunness | Rose Brothers Sports Ground, Gainsborough | Results |
| 12 Sep 1999 | | Laughton v Scunthorpe Town Fourth XI | Laughton Cricket Ground, Laughton | Results |
| 19 Sep 1999 | | Appleby Frodingham Third XI v Gunness | Brumby Hall, Scunthorpe | Results |
| 19 Sep 1999 | | Burton Stather v Laughton | Burton Stather Cricket Ground, Burton Stather | Results |
| 19 Sep 1999 | | Scunthorpe Town Fourth XI v Beckingham | Co-operative Sports Ground, Scunthorpe | Results |
| 15 Aug 1999 | | Scunthorpe Town Fourth XI v Corringham | Co-operative Sports Ground, Scunthorpe | Results |
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