| 06 May 1959 | | Keadby Midweek XI v Haxey Midweek XI | Keadby Power Station Sports Ground, Keadby | Results |
| 06 May 1959 | | Outcasts Midweek XI v Epworth Midweek XI | Crowle | Results |
| 13 May 1959 | | Belton Midweek XI v Epworth Midweek Second XI | Church Street, Belton | Results |
| 13 May 1959 | | Epworth Midweek XI v Westwoodside Midweek XI | Carrside, Epworth | Results |
| 13 May 1959 | | Gunness Midweek XI v Owston Ferry Midweek XI | Gunness | Results |
| 13 May 1959 | | Haxey Midweek XI v Outcasts Midweek XI | Haxey Lane, Haxey | Results |
| 20 May 1959 | | Epworth Midweek Second XI v Gunness Midweek XI | Carrside, Epworth | Results |
| 20 May 1959 | | Keadby Midweek XI v Belton Midweek XI | Keadby Power Station Sports Ground, Keadby | Results |
| 20 May 1959 | | Owston Ferry Midweek XI v Sun Engineers Midweek XI | Owston Ferry Cricket Ground, Owston Ferry | Results |
| 20 May 1959 | | Westwoodside Midweek XI v Haxey Midweek XI | Westwoodside Playing Field, Westwoodside | Results |
| 27 May 1959 | | Belton Midweek XI v Outcasts Midweek XI | Church Street, Belton | Results |
| 27 May 1959 | | Epworth Midweek XI v Owston Ferry Midweek XI | Carrside, Epworth | Results |
| 27 May 1959 | | Keadby Midweek XI v Gunness Midweek XI | Keadby Power Station Sports Ground, Keadby | Results |
| 27 May 1959 | | Sun Engineers Midweek XI v Epworth Midweek Second XI | Crowle | Results |
| 03 Jun 1959 | | Epworth Midweek Second XI v Epworth Midweek XI | Carrside, Epworth | Results |
| 03 Jun 1959 | | Keadby Midweek XI v Sun Engineers Midweek XI | Keadby Power Station Sports Ground, Keadby | Results |
| 03 Jun 1959 | | Outcasts Midweek XI v Gunness Midweek XI | Crowle | Results |
| 03 Jun 1959 | | Owston Ferry Midweek XI v Haxey Midweek XI | Owston Ferry Cricket Ground, Owston Ferry | Results |
| 03 Jun 1959 | | Westwoodside Midweek XI v Belton Midweek XI | Westwoodside Playing Field, Westwoodside | Results |
| 10 Jun 1959 | | Epworth Midweek XI v Belton Midweek XI | Carrside, Epworth | Results |
| 10 Jun 1959 | | Gunness Midweek XI v Westwoodside Midweek XI | Gunness | Results |
| 10 Jun 1959 | | Haxey Midweek XI v Epworth Midweek Second XI | Haxey Lane, Haxey | Results |
| 10 Jun 1959 | | Sun Engineers Midweek XI v Outcasts Midweek XI | Crowle | Results |
| 17 Jun 1959 | | Epworth Midweek Second XI v Westwoodside Midweek XI | Carrside, Epworth | Results |
| 17 Jun 1959 | | Gunness Midweek XI v Haxey Midweek XI | Gunness | Results |
| 17 Jun 1959 | | Outcasts Midweek XI v Owston Ferry Midweek XI | Crowle | Results |
| 24 Jun 1959 | | Epworth Midweek Second XI v Outcasts Midweek XI | Carrside, Epworth | Results |
| 24 Jun 1959 | | Haxey Midweek XI v Epworth Midweek XI | Haxey Lane, Haxey | Results |
| 24 Jun 1959 | | Owston Ferry Midweek XI v Keadby Midweek XI | Owston Ferry Cricket Ground, Owston Ferry | Results |
| 24 Jun 1959 | | Sun Engineers Midweek XI v Gunness Midweek XI | Crowle | Results |
| 01 Jul 1959 | | Epworth Midweek XI v Sun Engineers Midweek XI | Carrside, Epworth | Results |
| 01 Jul 1959 | | Gunness Midweek XI v Belton Midweek XI | Gunness | Results |
| 01 Jul 1959 | | Keadby Midweek XI v Epworth Midweek Second XI | Keadby Power Station Sports Ground, Keadby | Results |
| 01 Jul 1959 | | Outcasts Midweek XI v Westwoodside Midweek XI | Crowle | Results |
| 08 Jul 1959 | | Belton Midweek XI v Haxey Midweek XI | Church Street, Belton | Results |
| 08 Jul 1959 | | Epworth Midweek XI v Gunness Midweek XI | Carrside, Epworth | Results |
| 08 Jul 1959 | | Keadby Midweek XI v Outcasts Midweek XI | Keadby Power Station Sports Ground, Keadby | Results |
| 08 Jul 1959 | | Owston Ferry Midweek XI v Epworth Midweek Second XI | Owston Ferry Cricket Ground, Owston Ferry | Results |
| 08 Jul 1959 | | Westwoodside Midweek XI v Sun Engineers Midweek XI | Westwoodside Playing Field, Westwoodside | Results |
| 15 Jul 1959 | | Haxey Midweek XI v Sun Engineers Midweek XI | Haxey Lane, Haxey | Results |
| 15 Jul 1959 | | Owston Ferry Midweek XI v Belton Midweek XI | Owston Ferry Cricket Ground, Owston Ferry | Results |
| 15 Jul 1959 | | Westwoodside Midweek XI v Keadby Midweek XI | Westwoodside Playing Field, Westwoodside | Results |
| 22 Jul 1959 | | Epworth Midweek XI v Keadby Midweek XI | Carrside, Epworth | Results |
| 22 Jul 1959 | | Sun Engineers Midweek XI v Belton Midweek XI | Crowle | Results |
| 22 Jul 1959 | | Westwoodside Midweek XI v Owston Ferry Midweek XI | Westwoodside Playing Field, Westwoodside | Results |
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