| 26 Apr 1969 | | Redbourn Works v Cleethorpes | Cemetery Road Sports Ground, Brumby | Results |
| 03 May 1969 | | Boston v Appleby Frodingham | Mayflower Sports Ground, Boston | Results |
| 03 May 1969 | | Cleethorpes v Ross Sports | Sports Ground, Cleethorpes | Results |
| 03 May 1969 | | Grimsby Town v Scunthorpe Town Second XI | Augusta Street, Grimsby | Results |
| 03 May 1969 | | Immingham British Rail Sports Association v Lincoln Claytons | Blossom Way, Immingham | Results |
| 03 May 1969 | | Paper Mills v Ruston Bucyrus | Drewery Brothers Ground, Grimsby | Results |
| 03 May 1969 | | Redbourn Works v Lysaghts | Cemetery Road Sports Ground, Brumby | Results |
| 04 May 1969 | | Grimsby British Rail Sports Association v Redbourn Works | Carr Lane, Grimsby | Results |
| 10 May 1969 | | Appleby Frodingham v Immingham British Rail Sports Association | Brumby Hall, Scunthorpe | Results |
| 10 May 1969 | | Barton Town v Normanby Park | Marsh Lane, Barton on Humber | Results |
| 10 May 1969 | | Boston v Healing Clee Rovers | Mayflower Sports Ground, Boston | Results |
| 10 May 1969 | | Grimsby Town v Cleethorpes | Augusta Street, Grimsby | Results |
| 10 May 1969 | | Ruston Bucyrus v Grimsby British Rail Sports Association | Ruston-Bucyrus Ground, Lincoln | Results |
| 10 May 1969 | | Lysaghts v Lincoln Claytons | Cemetery Road Sports Ground, Brumby | Results |
| 10 May 1969 | | Paper Mills v Redbourn Works | Drewery Brothers Ground, Grimsby | Results |
| 10 May 1969 | | Scunthorpe Town Second XI v Ross Sports | Heslam Park, Scunthorpe | Results |
| 17 May 1969 | | Ross Sports v Scunthorpe Town Second XI | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 17 May 1969 | | Appleby Frodingham v Healing Clee Rovers | Brumby Hall, Scunthorpe | Results |
| 17 May 1969 | | Barton Town v Grimsby Town | Marsh Lane, Barton on Humber | Results |
| 17 May 1969 | | Immingham British Rail Sports Association v Cleethorpes | Blossom Way, Immingham | Results |
| 17 May 1969 | | Ruston Bucyrus v Normanby Park | Ruston-Bucyrus Ground, Lincoln | Results |
| 17 May 1969 | | Lysaghts v Paper Mills | Cemetery Road Sports Ground, Brumby | Results |
| 17 May 1969 | | Redbourn Works v Grimsby British Rail Sports Association | Cemetery Road Sports Ground, Brumby | Results |
| 18 May 1969 | | Grimsby British Rail Sports Association v Normanby Park | Carr Lane, Grimsby | Results |
| 24 May 1969 | | Healing Clee Rovers v Grimsby British Rail Sports Association | Oak Road, Healing | Results |
| 24 May 1969 | | Grimsby Town v Ruston Bucyrus | Augusta Street, Grimsby | Results |
| 24 May 1969 | | Lincoln Claytons v Appleby Frodingham | Clayton's Sports Club Ground, Lincoln | Results |
| 24 May 1969 | | Lysaghts v Boston | Cemetery Road Sports Ground, Brumby | Results |
| 24 May 1969 | | Normanby Park v Immingham British Rail Sports Association | Normanby Park Estate, Scunthorpe | Results |
| 24 May 1969 | | Paper Mills v Barton Town | Drewery Brothers Ground, Grimsby | Results |
| 24 May 1969 | | Ross Sports v Redbourn Works | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 24 May 1969 | | Scunthorpe Town Second XI v Cleethorpes | Heslam Park, Scunthorpe | Results |
| 26 May 1969 | | Grimsby British Rail Sports Association v Barton Town | Carr Lane, Grimsby | Results |
| 26 May 1969 | | Cleethorpes v Grimsby Town | Sports Ground, Cleethorpes | Results |
| 26 May 1969 | | Ruston Bucyrus v Lysaghts | Ruston-Bucyrus Ground, Lincoln | Results |
| 26 May 1969 | | Normanby Park v Healing Clee Rovers | Normanby Park Estate, Scunthorpe | Results |
| 26 May 1969 | | Redbourn Works v Paper Mills | Cemetery Road Sports Ground, Brumby | Results |
| 26 May 1969 | | Scunthorpe Town Second XI v Appleby Frodingham | Heslam Park, Scunthorpe | Results |
| 31 May 1969 | | Healing Clee Rovers v Ross Sports | Oak Road, Healing | Results |
| 31 May 1969 | | Cleethorpes v Normanby Park | Sports Ground, Cleethorpes | Results |
| 31 May 1969 | | Immingham British Rail Sports Association v Grimsby Town | Blossom Way, Immingham | Results |
| 31 May 1969 | | Ruston Bucyrus v Lincoln Claytons | Ruston-Bucyrus Ground, Lincoln | Results |
| 31 May 1969 | | Lysaghts v Appleby Frodingham | Cemetery Road Sports Ground, Brumby | Results |
| 31 May 1969 | | Paper Mills v Scunthorpe Town Second XI | Drewery Brothers Ground, Grimsby | Results |
| 31 May 1969 | | Redbourn Works v Barton Town | Cemetery Road Sports Ground, Brumby | Results |
| 01 Jun 1969 | | Boston v Lysaghts | Mayflower Sports Ground, Boston | Results |
| 07 Jun 1969 | | Grimsby British Rail Sports Association v Ruston Bucyrus | Carr Lane, Grimsby | Results |
| 07 Jun 1969 | | Healing Clee Rovers v Boston | Oak Road, Healing | Results |
| 07 Jun 1969 | | Immingham British Rail Sports Association v Lysaghts | Blossom Way, Immingham | Results |
| 07 Jun 1969 | | Normanby Park v Scunthorpe Town Second XI | Normanby Park Estate, Scunthorpe | Results |
| 07 Jun 1969 | | Paper Mills v Appleby Frodingham | Drewery Brothers Ground, Grimsby | Results |
| 07 Jun 1969 | | Redbourn Works v Grimsby Town | Cemetery Road Sports Ground, Brumby | Results |
| 07 Jun 1969 | | Ross Sports v Barton Town | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 14 Jun 1969 | | Appleby Frodingham v Normanby Park | Brumby Hall, Scunthorpe | Results |
| 14 Jun 1969 | | Barton Town v Redbourn Works | Marsh Lane, Barton on Humber | Results |
| 14 Jun 1969 | | Grimsby British Rail Sports Association v Healing Clee Rovers | Carr Lane, Grimsby | Results |
| 14 Jun 1969 | | Grimsby Town v Immingham British Rail Sports Association | Augusta Street, Grimsby | Results |
| 14 Jun 1969 | | Lincoln Claytons v Paper Mills | Clayton's Sports Club Ground, Lincoln | Results |
| 14 Jun 1969 | | Lysaghts v Scunthorpe Town Second XI | Cemetery Road Sports Ground, Brumby | Results |
| 14 Jun 1969 | | Ross Sports v Cleethorpes | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 21 Jun 1969 | | Appleby Frodingham v Ruston Bucyrus | Brumby Hall, Scunthorpe | Results |
| 21 Jun 1969 | | Healing Clee Rovers v Barton Town | Oak Road, Healing | Results |
| 21 Jun 1969 | | Grimsby Town v Paper Mills | Augusta Street, Grimsby | Results |
| 21 Jun 1969 | | Lysaghts v Normanby Park | Cemetery Road Sports Ground, Brumby | Results |
| 21 Jun 1969 | | Redbourn Works v Boston | Cemetery Road Sports Ground, Brumby | Results |
| 21 Jun 1969 | | Ross Sports v Lincoln Claytons | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 21 Jun 1969 | | Scunthorpe Town Second XI v Immingham British Rail Sports Association | Heslam Park, Scunthorpe | Results |
| 22 Jun 1969 | | Boston v Lincoln Claytons | Mayflower Sports Ground, Boston | Results |
| 28 Jun 1969 | | Appleby Frodingham v Ross Sports | Brumby Hall, Scunthorpe | Results |
| 28 Jun 1969 | | Cleethorpes v Ruston Bucyrus | Sports Ground, Cleethorpes | Results |
| 28 Jun 1969 | | Grimsby Town v Barton Town | Augusta Street, Grimsby | Results |
| 28 Jun 1969 | | Immingham British Rail Sports Association v Grimsby British Rail Sports Association | Blossom Way, Immingham | Results |
| 28 Jun 1969 | | Lincoln Claytons v Healing Clee Rovers | Clayton's Sports Club Ground, Lincoln | Results |
| 28 Jun 1969 | | Paper Mills v Lysaghts | Drewery Brothers Ground, Grimsby | Results |
| 28 Jun 1969 | | Scunthorpe Town Second XI v Normanby Park | Heslam Park, Scunthorpe | Results |
| 29 Jun 1969 | | Ruston Bucyrus v Grimsby Town | Ruston-Bucyrus Ground, Lincoln | Results |
| 05 Jul 1969 | | Barton Town v Boston | Marsh Lane, Barton on Humber | Results |
| 05 Jul 1969 | | Grimsby British Rail Sports Association v Scunthorpe Town Second XI | Carr Lane, Grimsby | Results |
| 05 Jul 1969 | | Healing Clee Rovers v Appleby Frodingham | Oak Road, Healing | Results |
| 05 Jul 1969 | | Grimsby Town v Redbourn Works | Augusta Street, Grimsby | Results |
| 05 Jul 1969 | | Immingham British Rail Sports Association v Ruston Bucyrus | Blossom Way, Immingham | Results |
| 05 Jul 1969 | | Normanby Park v Ross Sports | Normanby Park Estate, Scunthorpe | Results |
| 06 Jul 1969 | | Lincoln Claytons v Boston | Clayton's Sports Club Ground, Lincoln | Results |
| 06 Jul 1969 | | Normanby Park v Redbourn Works | Normanby Park Estate, Scunthorpe | Results |
| 12 Jul 1969 | | Appleby Frodingham v Grimsby British Rail Sports Association | Brumby Hall, Scunthorpe | Results |
| 12 Jul 1969 | | Cleethorpes v Healing Clee Rovers | Sports Ground, Cleethorpes | Results |
| 12 Jul 1969 | | Lysaghts v Barton Town | Cemetery Road Sports Ground, Brumby | Results |
| 12 Jul 1969 | | Normanby Park v Paper Mills | Normanby Park Estate, Scunthorpe | Results |
| 12 Jul 1969 | | Redbourn Works v Scunthorpe Town Second XI | Cemetery Road Sports Ground, Brumby | Results |
| 12 Jul 1969 | | Ross Sports v Grimsby Town | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 13 Jul 1969 | | Lincoln Claytons v Lysaghts | Clayton's Sports Club Ground, Lincoln | Results |
| 19 Jul 1969 | | Ruston Bucyrus v Immingham British Rail Sports Association | Ruston-Bucyrus Ground, Lincoln | Results |
| 19 Jul 1969 | | Lysaghts v Grimsby British Rail Sports Association | Cemetery Road Sports Ground, Brumby | Results |
| 19 Jul 1969 | | Normanby Park v Barton Town | Normanby Park Estate, Scunthorpe | Results |
| 19 Jul 1969 | | Paper Mills v Healing Clee Rovers | Drewery Brothers Ground, Grimsby | Results |
| 19 Jul 1969 | | Ross Sports v Appleby Frodingham | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 19 Jul 1969 | | Scunthorpe Town Second XI v Grimsby Town | Heslam Park, Scunthorpe | Results |
| 20 Jul 1969 | | Lincoln Claytons v Ruston Bucyrus | Clayton's Sports Club Ground, Lincoln | Results |
| 26 Jul 1969 | | Barton Town v Appleby Frodingham | Marsh Lane, Barton on Humber | Results |
| 26 Jul 1969 | | Boston v Grimsby Town | Mayflower Sports Ground, Boston | Results |
| 26 Jul 1969 | | Grimsby British Rail Sports Association v Paper Mills | Carr Lane, Grimsby | Results |
| 26 Jul 1969 | | Healing Clee Rovers v Lysaghts | Oak Road, Healing | Results |
| 26 Jul 1969 | | Ruston Bucyrus v Ross Sports | Ruston-Bucyrus Ground, Lincoln | Results |
| 26 Jul 1969 | | Lincoln Claytons v Scunthorpe Town Second XI | Clayton's Sports Club Ground, Lincoln | Results |
| 26 Jul 1969 | | Redbourn Works v Immingham British Rail Sports Association | Cemetery Road Sports Ground, Brumby | Results |
| 27 Jul 1969 | | Cleethorpes v Paper Mills | Sports Ground, Cleethorpes | Results |
| 02 Aug 1969 | | Appleby Frodingham v Grimsby Town | Brumby Hall, Scunthorpe | Results |
| 02 Aug 1969 | | Barton Town v Lysaghts | Marsh Lane, Barton on Humber | Results |
| 02 Aug 1969 | | Boston v Grimsby British Rail Sports Association | Mayflower Sports Ground, Boston | Results |
| 02 Aug 1969 | | Healing Clee Rovers v Scunthorpe Town Second XI | Oak Road, Healing | Results |
| 02 Aug 1969 | | Immingham British Rail Sports Association v Redbourn Works | Blossom Way, Immingham | Results |
| 02 Aug 1969 | | Lincoln Claytons v Cleethorpes | Clayton's Sports Club Ground, Lincoln | Results |
| 02 Aug 1969 | | Normanby Park v Ruston Bucyrus | Normanby Park Estate, Scunthorpe | Results |
| 02 Aug 1969 | | Ross Sports v Paper Mills | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 03 Aug 1969 | | Immingham British Rail Sports Association v Boston | Blossom Way, Immingham | Results |
| 09 Aug 1969 | | Appleby Frodingham v Paper Mills | Brumby Hall, Scunthorpe | Results |
| 09 Aug 1969 | | Grimsby Town v Healing Clee Rovers | Augusta Street, Grimsby | Results |
| 09 Aug 1969 | | Immingham British Rail Sports Association v Scunthorpe Town Second XI | Blossom Way, Immingham | Results |
| 09 Aug 1969 | | Ruston Bucyrus v Barton Town | Ruston-Bucyrus Ground, Lincoln | Results |
| 09 Aug 1969 | | Lysaghts v Cleethorpes | Cemetery Road Sports Ground, Brumby | Results |
| 09 Aug 1969 | | Normanby Park v Lincoln Claytons | Normanby Park Estate, Scunthorpe | Results |
| 09 Aug 1969 | | Ross Sports v Boston | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 10 Aug 1969 | | Boston v Barton Town | Mayflower Sports Ground, Boston | Results |
| 10 Aug 1969 | | Lincoln Claytons v Redbourn Works | Clayton's Sports Club Ground, Lincoln | Results |
| 16 Aug 1969 | | Barton Town v Lincoln Claytons | Marsh Lane, Barton on Humber | Results |
| 16 Aug 1969 | | Boston v Normanby Park | Mayflower Sports Ground, Boston | Results |
| 16 Aug 1969 | | Healing Clee Rovers v Immingham British Rail Sports Association | Oak Road, Healing | Results |
| 16 Aug 1969 | | Cleethorpes v Appleby Frodingham | Sports Ground, Cleethorpes | Results |
| 16 Aug 1969 | | Paper Mills v Grimsby Town | Drewery Brothers Ground, Grimsby | Results |
| 16 Aug 1969 | | Ross Sports v Grimsby British Rail Sports Association | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 16 Aug 1969 | | Scunthorpe Town Second XI v Ruston Bucyrus | Heslam Park, Scunthorpe | Results |
| 23 Aug 1969 | | Healing Clee Rovers v Ruston Bucyrus | Oak Road, Healing | Results |
| 23 Aug 1969 | | Immingham British Rail Sports Association v Paper Mills | Blossom Way, Immingham | Results |
| 23 Aug 1969 | | Lincoln Claytons v Grimsby British Rail Sports Association | Clayton's Sports Club Ground, Lincoln | Results |
| 23 Aug 1969 | | Lysaghts v Ross Sports | Cemetery Road Sports Ground, Brumby | Results |
| 23 Aug 1969 | | Redbourn Works v Appleby Frodingham | Cemetery Road Sports Ground, Brumby | Results |
| 23 Aug 1969 | | Scunthorpe Town Second XI v Boston | Heslam Park, Scunthorpe | Results |
| 23 Aug 1969 | | Barton Town v Cleethorpes | Marsh Lane, Barton on Humber | Results |
| 23 Aug 1969 | | Grimsby Town v Normanby Park | Augusta Street, Grimsby | Results |
| 24 Aug 1969 | | Redbourn Works v Lincoln Claytons | Cemetery Road Sports Ground, Brumby | Results |
| 30 Aug 1969 | | Appleby Frodingham v Lincoln Claytons | Brumby Hall, Scunthorpe | Results |
| 30 Aug 1969 | | Barton Town v Scunthorpe Town Second XI | Marsh Lane, Barton on Humber | Results |
| 30 Aug 1969 | | Grimsby British Rail Sports Association v Immingham British Rail Sports Association | Carr Lane, Grimsby | Results |
| 30 Aug 1969 | | Healing Clee Rovers v Grimsby Town | Oak Road, Healing | Results |
| 30 Aug 1969 | | Cleethorpes v Boston | Sports Ground, Cleethorpes | Results |
| 30 Aug 1969 | | Ruston Bucyrus v Redbourn Works | Ruston-Bucyrus Ground, Lincoln | Results |
| 30 Aug 1969 | | Paper Mills v Ross Sports | Drewery Brothers Ground, Grimsby | Results |
| 31 Aug 1969 | | Paper Mills v Cleethorpes | Drewery Brothers Ground, Grimsby | Results |
| 01 Sep 1969 | | Appleby Frodingham v Scunthorpe Town Second XI | Brumby Hall, Scunthorpe | Results |
| 01 Sep 1969 | | Barton Town v Immingham British Rail Sports Association | Marsh Lane, Barton on Humber | Results |
| 01 Sep 1969 | | Boston v Paper Mills | Mayflower Sports Ground, Boston | Results |
| 01 Sep 1969 | | Grimsby British Rail Sports Association v Grimsby Town | Carr Lane, Grimsby | Results |
| 06 Sep 1969 | | Cleethorpes v Grimsby British Rail Sports Association | Sports Ground, Cleethorpes | Results |
| 06 Sep 1969 | | Grimsby Town v Lincoln Claytons | Augusta Street, Grimsby | Results |
| 06 Sep 1969 | | Ruston Bucyrus v Boston | Ruston-Bucyrus Ground, Lincoln | Results |
| 06 Sep 1969 | | Normanby Park v Lysaghts | Normanby Park Estate, Scunthorpe | Results |
| 06 Sep 1969 | | Redbourn Works v Healing Clee Rovers | Cemetery Road Sports Ground, Brumby | Results |
| 06 Sep 1969 | | Ross Sports v Immingham British Rail Sports Association | Ross Sports Club Ground, Weelsby Road, Grimsby | Results |
| 07 Sep 1969 | | Grimsby British Rail Sports Association v Lysaghts | Carr Lane, Grimsby | Results |
| 07 Sep 1969 | | Grimsby Town v Boston | Augusta Street, Grimsby | Results |
| 13 Sep 1969 | | Paper Mills v Normanby Park | Drewery Brothers Ground, Grimsby | Results |
| 13 Sep 1969 | | Grimsby Town v Ross Sports | Augusta Street, Grimsby | Results |
| 13 Sep 1969 | | Lysaghts v Immingham British Rail Sports Association | Cemetery Road Sports Ground, Brumby | Results |
| 14 Sep 1969 | | Lysaghts v Grimsby Town | Cemetery Road Sports Ground, Brumby | Results |
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