| 24 Apr 1999 | | Haxey v Hykeham | Haxey Lane, Haxey | Results |
| 24 Apr 1999 | | Nettleham v Brigg Town | Mulsanne Park, Nettleham | Results |
| 24 Apr 1999 | | Scunthorpe Town v Horncastle | Heslam Park, Scunthorpe | Results |
| 01 May 1999 | | Bottesford Town v Horncastle | Birch Park, Bottesford | Results |
| 01 May 1999 | | Louth v Millennium Chemicals | London Road, Louth | Results |
| 01 May 1999 | | Scunthorpe Town v Haxey | Heslam Park, Scunthorpe | Results |
| 08 May 1999 | | Haxey v Bottesford Town | Haxey Lane, Haxey | Results |
| 08 May 1999 | | Horncastle v Brigg Town | Coronation Walk, Horncastle | Results |
| 08 May 1999 | | Louth v Cleethorpes Third XI | London Road, Louth | Results |
| 08 May 1999 | | Millennium Chemicals v Hykeham | Clee Road, Grimsby | Results |
| 09 May 1999 | | Cleethorpes Third XI v Nettleham | Sports Ground, Cleethorpes | Results |
| 15 May 1999 | | Brigg Town v Haxey | Brigg Recreation Ground, Brigg | Results |
| 15 May 1999 | | Hykeham v Louth | Memorial Field, North Hykeham | Results |
| 15 May 1999 | | Nettleham v Horncastle | Mulsanne Park, Nettleham | Results |
| 15 May 1999 | | Scunthorpe Town v Millennium Chemicals | Heslam Park, Scunthorpe | Results |
| 22 May 1999 | | Cleethorpes Third XI v Hykeham | Sports Ground, Cleethorpes | Results |
| 22 May 1999 | | Haxey v Nettleham | Haxey Lane, Haxey | Results |
| 22 May 1999 | | Louth v Scunthorpe Town | London Road, Louth | Results |
| 22 May 1999 | | Millennium Chemicals v Bottesford Town | Clee Road, Grimsby | Results |
| 29 May 1999 | | Bottesford Town v Louth | Birch Park, Bottesford | Results |
| 29 May 1999 | | Brigg Town v Millennium Chemicals | Brigg Recreation Ground, Brigg | Results |
| 29 May 1999 | | Horncastle v Cleethorpes Third XI | Coronation Walk, Horncastle | Results |
| 29 May 1999 | | Scunthorpe Town v Hykeham | Heslam Park, Scunthorpe | Results |
| 05 Jun 1999 | | Cleethorpes Third XI v Scunthorpe Town | Sports Ground, Cleethorpes | Results |
| 05 Jun 1999 | | Haxey v Horncastle | Haxey Lane, Haxey | Results |
| 05 Jun 1999 | | Hykeham v Bottesford Town | Memorial Field, North Hykeham | Results |
| 05 Jun 1999 | | Louth v Brigg Town | London Road, Louth | Results |
| 05 Jun 1999 | | Millennium Chemicals v Nettleham | Clee Road, Grimsby | Results |
| 12 Jun 1999 | | Bottesford Town v Scunthorpe Town | Birch Park, Bottesford | Results |
| 12 Jun 1999 | | Brigg Town v Hykeham | Brigg Recreation Ground, Brigg | Results |
| 12 Jun 1999 | | Haxey v Cleethorpes Third XI | Haxey Lane, Haxey | Results |
| 12 Jun 1999 | | Nettleham v Louth | Mulsanne Park, Nettleham | Results |
| 13 Jun 1999 | | Millennium Chemicals v Cleethorpes Third XI | Clee Road, Grimsby | Results |
| 19 Jun 1999 | | Cleethorpes Third XI v Bottesford Town | Sports Ground, Cleethorpes | Results |
| 19 Jun 1999 | | Hykeham v Nettleham | Memorial Field, North Hykeham | Results |
| 19 Jun 1999 | | Millennium Chemicals v Horncastle | Clee Road, Grimsby | Results |
| 19 Jun 1999 | | Scunthorpe Town v Brigg Town | Heslam Park, Scunthorpe | Results |
| 20 Jun 1999 | | Cleethorpes Third XI v Louth | Sports Ground, Cleethorpes | Results |
| 26 Jun 1999 | | Brigg Town v Bottesford Town | Brigg Recreation Ground, Brigg | Results |
| 26 Jun 1999 | | Haxey v Millennium Chemicals | Haxey Lane, Haxey | Results |
| 26 Jun 1999 | | Horncastle v Louth | Coronation Walk, Horncastle | Results |
| 26 Jun 1999 | | Nettleham v Scunthorpe Town | Mulsanne Park, Nettleham | Results |
| 27 Jun 1999 | | Cleethorpes Third XI v Brigg Town | Sports Ground, Cleethorpes | Results |
| 03 Jul 1999 | | Bottesford Town v Nettleham | Birch Park, Bottesford | Results |
| 03 Jul 1999 | | Hykeham v Horncastle | Memorial Field, North Hykeham | Results |
| 03 Jul 1999 | | Louth v Haxey | London Road, Louth | Results |
| 04 Jul 1999 | | Cleethorpes Third XI v Millennium Chemicals | Sports Ground, Cleethorpes | Results |
| 10 Jul 1999 | | Bottesford Town v Hykeham | Birch Park, Bottesford | Results |
| 10 Jul 1999 | | Brigg Town v Louth | Brigg Recreation Ground, Brigg | Results |
| 10 Jul 1999 | | Horncastle v Haxey | Coronation Walk, Horncastle | Results |
| 10 Jul 1999 | | Nettleham v Millennium Chemicals | Mulsanne Park, Nettleham | Results |
| 10 Jul 1999 | | Scunthorpe Town v Cleethorpes Third XI | Heslam Park, Scunthorpe | Results |
| 17 Jul 1999 | | Hykeham v Brigg Town | Memorial Field, North Hykeham | Results |
| 17 Jul 1999 | | Louth v Nettleham | London Road, Louth | Results |
| 17 Jul 1999 | | Scunthorpe Town v Bottesford Town | Heslam Park, Scunthorpe | Results |
| 24 Jul 1999 | | Bottesford Town v Cleethorpes Third XI | Birch Park, Bottesford | Results |
| 24 Jul 1999 | | Brigg Town v Scunthorpe Town | Brigg Recreation Ground, Brigg | Results |
| 24 Jul 1999 | | Horncastle v Millennium Chemicals | Coronation Walk, Horncastle | Results |
| 24 Jul 1999 | | Nettleham v Hykeham | Mulsanne Park, Nettleham | Results |
| 31 Jul 1999 | | Bottesford Town v Brigg Town | Birch Park, Bottesford | Results |
| 31 Jul 1999 | | Louth v Horncastle | London Road, Louth | Results |
| 31 Jul 1999 | | Millennium Chemicals v Haxey | Clee Road, Grimsby | Results |
| 31 Jul 1999 | | Scunthorpe Town v Nettleham | Heslam Park, Scunthorpe | Results |
| 07 Aug 1999 | | Brigg Town v Cleethorpes Third XI | Brigg Recreation Ground, Brigg | Results |
| 07 Aug 1999 | | Haxey v Louth | Haxey Lane, Haxey | Results |
| 07 Aug 1999 | | Horncastle v Hykeham | Coronation Walk, Horncastle | Results |
| 07 Aug 1999 | | Nettleham v Bottesford Town | Mulsanne Park, Nettleham | Results |
| 14 Aug 1999 | | Cleethorpes Third XI v Haxey | Sports Ground, Cleethorpes | Results |
| 14 Aug 1999 | | Hykeham v Scunthorpe Town | Memorial Field, North Hykeham | Results |
| 14 Aug 1999 | | Louth v Bottesford Town | London Road, Louth | Results |
| 14 Aug 1999 | | Millennium Chemicals v Brigg Town | Clee Road, Grimsby | Results |
| 21 Aug 1999 | | Bottesford Town v Millennium Chemicals | Birch Park, Bottesford | Results |
| 21 Aug 1999 | | Hykeham v Cleethorpes Third XI | Memorial Field, North Hykeham | Results |
| 21 Aug 1999 | | Nettleham v Haxey | Mulsanne Park, Nettleham | Results |
| 21 Aug 1999 | | Scunthorpe Town v Louth | Heslam Park, Scunthorpe | Results |
| 22 Aug 1999 | | Cleethorpes Third XI v Horncastle | Sports Ground, Cleethorpes | Results |
| 28 Aug 1999 | | Haxey v Brigg Town | Haxey Lane, Haxey | Results |
| 28 Aug 1999 | | Horncastle v Nettleham | Coronation Walk, Horncastle | Results |
| 28 Aug 1999 | | Louth v Hykeham | London Road, Louth | Results |
| 28 Aug 1999 | | Millennium Chemicals v Scunthorpe Town | Clee Road, Grimsby | Results |
| 30 Aug 1999 | | Bottesford Town v Haxey | Birch Park, Bottesford | Results |
| 30 Aug 1999 | | Brigg Town v Horncastle | Brigg Recreation Ground, Brigg | Results |
| 30 Aug 1999 | | Hykeham v Millennium Chemicals | Memorial Field, North Hykeham | Results |
| 04 Sep 1999 | | Haxey v Scunthorpe Town | Haxey Lane, Haxey | Results |
| 04 Sep 1999 | | Horncastle v Bottesford Town | Coronation Walk, Horncastle | Results |
| 04 Sep 1999 | | Millennium Chemicals v Louth | Clee Road, Grimsby | Results |
| 04 Sep 1999 | | Nettleham v Cleethorpes Third XI | Mulsanne Park, Nettleham | Results |
| 11 Sep 1999 | | Brigg Town v Nettleham | Brigg Recreation Ground, Brigg | Results |
| 11 Sep 1999 | | Horncastle v Scunthorpe Town | Coronation Walk, Horncastle | Results |
| 11 Sep 1999 | | Hykeham v Haxey | Memorial Field, North Hykeham | Results |
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