| 18 Apr 1896 | | Redcar v North Ormesby | Coatham Road, Redcar | Results |
| 18 Apr 1896 | | Thornaby v Guisborough | Mandale Bottoms, Thornaby | Results |
| 25 Apr 1896 | | Redcar v Thornaby | Coatham Road, Redcar | Results |
| 02 May 1896 | | Ironopolis v Redcar | Middlesbrough | Results |
| 02 May 1896 | | North Ormesby v Guisborough | Vicarage Ground, North Ormesby, Middlesbrough | Results |
| 02 May 1896 | | Thornaby v Stockton | Mandale Bottoms, Thornaby | Results |
| 02 May 1896 | | Darlington v Northallerton | Feethams Cricket Ground, Darlington | Results |
| 02 May 1896 | | Thirsk v Middlesbrough | Racecourse Ground, Thirsk | Results |
| 09 May 1896 | | North Ormesby v Redcar | Vicarage Ground, North Ormesby, Middlesbrough | Results |
| 09 May 1896 | | Guisborough v Thornaby | Fountains Garth, Guisborough | Results |
| 09 May 1896 | | Northallerton v Thirsk | Farndale Avenue, Northallerton | Results |
| 09 May 1896 | | Stockton v Darlington | Grangefield Road, Stockton-on-Tees | Results |
| 09 May 1896 | | Middlesbrough v Ironopolis | Acklam Park, Middlesbrough | Results |
| 16 May 1896 | | Redcar v Ironopolis | Coatham Road, Redcar | Results |
| 16 May 1896 | | North Ormesby v Northallerton | Vicarage Ground, North Ormesby, Middlesbrough | Results |
| 16 May 1896 | | Middlesbrough v Thornaby | Acklam Park, Middlesbrough | Results |
| 23 May 1896 | | Thornaby v Redcar | Mandale Bottoms, Thornaby | Results |
| 23 May 1896 | | Middlesbrough v North Ormesby | Acklam Park, Middlesbrough | Results |
| 23 May 1896 | | Northallerton v Stockton | Farndale Avenue, Northallerton | Results |
| 23 May 1896 | | Ironopolis v Darlington | Middlesbrough | Results |
| 25 May 1896 | | North Ormesby v Thornaby | Vicarage Ground, North Ormesby, Middlesbrough | Results |
| 26 May 1896 | | Thirsk v North Ormesby | Racecourse Ground, Thirsk | Results |
| 26 May 1896 | | Darlington v Thornaby | Feethams Cricket Ground, Darlington | Results |
| 26 May 1896 | | Middlesbrough v Stockton | Acklam Park, Middlesbrough | Results |
| 30 May 1896 | | Stockton v Redcar | Grangefield Road, Stockton-on-Tees | Results |
| 30 May 1896 | | North Ormesby v Thirsk | Vicarage Ground, North Ormesby, Middlesbrough | Results |
| 30 May 1896 | | Ironopolis v Thornaby | Middlesbrough | Results |
| 30 May 1896 | | Guisborough v Middlesbrough | Fountains Garth, Guisborough | Results |
| 06 Jun 1896 | | Middlesbrough v Redcar | Acklam Park, Middlesbrough | Results |
| 06 Jun 1896 | | North Ormesby v Stockton | Vicarage Ground, North Ormesby, Middlesbrough | Results |
| 06 Jun 1896 | | Northallerton v Thornaby | Farndale Avenue, Northallerton | Results |
| 06 Jun 1896 | | Ironopolis v Guisborough | Middlesbrough | Results |
| 06 Jun 1896 | | Thirsk v Darlington | Racecourse Ground, Thirsk | Results |
| 13 Jun 1896 | | Thornaby v Ironopolis | Mandale Bottoms, Thornaby | Results |
| 13 Jun 1896 | | Thirsk v Guisborough | Racecourse Ground, Thirsk | Results |
| 13 Jun 1896 | | Stockton v Northallerton | Grangefield Road, Stockton-on-Tees | Results |
| 13 Jun 1896 | | Darlington v Middlesbrough | Feethams Cricket Ground, Darlington | Results |
| 20 Jun 1896 | | Guisborough v Redcar | Fountains Garth, Guisborough | Results |
| 20 Jun 1896 | | North Ormesby v Darlington | Vicarage Ground, North Ormesby, Middlesbrough | Results |
| 20 Jun 1896 | | Thornaby v Thirsk | Mandale Bottoms, Thornaby | Results |
| 20 Jun 1896 | | Northallerton v Middlesbrough | Farndale Avenue, Northallerton | Results |
| 20 Jun 1896 | | Ironopolis v Stockton | Middlesbrough | Results |
| 27 Jun 1896 | | Stockton v Guisborough | Grangefield Road, Stockton-on-Tees | Results |
| 27 Jun 1896 | | North Ormesby v Darlington | Vicarage Ground, North Ormesby, Middlesbrough | Results |
| 27 Jun 1896 | | Thirsk v Ironopolis | Racecourse Ground, Thirsk | Results |
| 04 Jul 1896 | | Thornaby v Northallerton | Mandale Bottoms, Thornaby | Results |
| 04 Jul 1896 | | Middlesbrough v Guisborough | Acklam Park, Middlesbrough | Results |
| 04 Jul 1896 | | Darlington v Stockton | Feethams Cricket Ground, Darlington | Results |
| 11 Jul 1896 | | Northallerton v Redcar | Farndale Avenue, Northallerton | Results |
| 11 Jul 1896 | | Thornaby v North Ormesby | Mandale Bottoms, Thornaby | Results |
| 11 Jul 1896 | | Guisborough v Ironopolis | Fountains Garth, Guisborough | Results |
| 11 Jul 1896 | | Middlesbrough v Darlington | Acklam Park, Middlesbrough | Results |
| 11 Jul 1896 | | Stockton v Thirsk | Grangefield Road, Stockton-on-Tees | Results |
| 18 Jul 1896 | | Guisborough v Stockton | Fountains Garth, Guisborough | Results |
| 18 Jul 1896 | | Thirsk v Northallerton | Racecourse Ground, Thirsk | Results |
| 18 Jul 1896 | | Darlington v Ironopolis | Feethams Cricket Ground, Darlington | Results |
| 25 Jul 1896 | | Redcar v Middlesbrough | Coatham Road, Redcar | Results |
| 25 Jul 1896 | | Darlington v North Ormesby | Feethams Cricket Ground, Darlington | Results |
| 25 Jul 1896 | | Stockton v Thornaby | Grangefield Road, Stockton-on-Tees | Results |
| 25 Jul 1896 | | Northallerton v Guisborough | Farndale Avenue, Northallerton | Results |
| 25 Jul 1896 | | Ironopolis v Thirsk | Middlesbrough | Results |
| 01 Aug 1896 | | Redcar v Stockton | Coatham Road, Redcar | Results |
| 01 Aug 1896 | | North Ormesby v Ironopolis | Vicarage Ground, North Ormesby, Middlesbrough | Results |
| 01 Aug 1896 | | Thornaby v Darlington | Mandale Bottoms, Thornaby | Results |
| 01 Aug 1896 | | Guisborough v Thirsk | Fountains Garth, Guisborough | Results |
| 01 Aug 1896 | | Middlesbrough v Northallerton | Acklam Park, Middlesbrough | Results |
| 03 Aug 1896 | | Redcar v Northallerton | Coatham Road, Redcar | Results |
| 03 Aug 1896 | | Stockton v Middlesbrough | Grangefield Road, Stockton-on-Tees | Results |
| 08 Aug 1896 | | Darlington v Guisborough | Feethams Cricket Ground, Darlington | Results |
| 08 Aug 1896 | | Northallerton v Ironopolis | Farndale Avenue, Northallerton | Results |
| 08 Aug 1896 | | Thirsk v Stockton | Racecourse Ground, Thirsk | Results |
| 15 Aug 1896 | | Redcar v Darlington | Coatham Road, Redcar | Results |
| 15 Aug 1896 | | Ironopolis v North Ormesby | Middlesbrough | Results |
| 15 Aug 1896 | | Guisborough v Northallerton | Fountains Garth, Guisborough | Results |
| 15 Aug 1896 | | Middlesbrough v Thirsk | Acklam Park, Middlesbrough | Results |
| 19 Aug 1896 | | Thirsk v Redcar | Racecourse Ground, Thirsk | Results |
| 21 Aug 1896 | | Stockton v North Ormesby | Grangefield Road, Stockton-on-Tees | Results |
| 21 Aug 1896 | | Thirsk v Thornaby | Racecourse Ground, Thirsk | Results |
| 22 Aug 1896 | | Darlington v Redcar | Feethams Cricket Ground, Darlington | Results |
| 22 Aug 1896 | | Guisborough v North Ormesby | Fountains Garth, Guisborough | Results |
| 22 Aug 1896 | | Thornaby v Middlesbrough | Mandale Bottoms, Thornaby | Results |
| 22 Aug 1896 | | Stockton v Ironopolis | Grangefield Road, Stockton-on-Tees | Results |
| 29 Aug 1896 | | Redcar v Guisborough | Coatham Road, Redcar | Results |
| 29 Aug 1896 | | Northallerton v North Ormesby | Farndale Avenue, Northallerton | Results |
| 29 Aug 1896 | | Darlington v Thirsk | Feethams Cricket Ground, Darlington | Results |
| 29 Aug 1896 | | Ironopolis v Middlesbrough | Middlesbrough | Results |
| 05 Sep 1896 | | Redcar v Thirsk | Coatham Road, Redcar | Results |
| 05 Sep 1896 | | North Ormesby v Middlesbrough | Vicarage Ground, North Ormesby, Middlesbrough | Results |
| 05 Sep 1896 | | Guisborough v Darlington | Fountains Garth, Guisborough | Results |
| 05 Sep 1896 | | Ironopolis v Northallerton | Middlesbrough | Results |
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