| 03 May 2009 | | Grimsby Town Development XI v Bottesford Town Second XI | Augusta Street, Grimsby | Results |
| 03 May 2009 | | Misterton Second XI v North Wheatley with Leverton Second XI | Marsh Lane, Misterton | Results |
| 03 May 2009 | | Upton cum Kexby v Barton Town Fourth XI | Upton cum Kexby Playing Field, Kexby | Results |
| 10 May 2009 | | Barton Town Fourth XI v Bottesford Town Second XI | Marsh Lane, Barton on Humber | Results |
| 10 May 2009 | | Everton Third XI v Grimsby Town Development XI | The Metcalfe Ground, Everton | Results |
| 10 May 2009 | | Upton cum Kexby v Misterton Second XI | Upton cum Kexby Playing Field, Kexby | Results |
| 17 May 2009 | | Bottesford Town Second XI v Everton Third XI | Birch Park, Bottesford | Results |
| 17 May 2009 | | Misterton Second XI v Barton Town Fourth XI | Marsh Lane, Misterton | Results |
| 17 May 2009 | | North Wheatley with Leverton Second XI v Grimsby Town Development XI | Playing Field, South Wheatley | Results |
| 24 May 2009 | | Barton Town Fourth XI v Upton cum Kexby | Marsh Lane, Barton on Humber | Results |
| 24 May 2009 | | Bottesford Town Second XI v Grimsby Town Development XI | Birch Park, Bottesford | Results |
| 24 May 2009 | | North Wheatley with Leverton Second XI v Misterton Second XI | Playing Field, South Wheatley | Results |
| 07 Jun 2009 | | Barton Town Fourth XI v Everton Third XI | Marsh Lane, Barton on Humber | Results |
| 07 Jun 2009 | | Grimsby Town Development XI v Misterton Second XI | Augusta Street, Grimsby | Results |
| 07 Jun 2009 | | Upton cum Kexby v North Wheatley with Leverton Second XI | Upton cum Kexby Playing Field, Kexby | Results |
| 14 Jun 2009 | | Barton Town Fourth XI v Grimsby Town Development XI | Marsh Lane, Barton on Humber | Results |
| 14 Jun 2009 | | North Wheatley with Leverton Second XI v Everton Third XI | Playing Field, South Wheatley | Results |
| 14 Jun 2009 | | Upton cum Kexby v Bottesford Town Second XI | Upton cum Kexby Playing Field, Kexby | Results |
| 28 Jun 2009 | | Bottesford Town Second XI v Misterton Second XI | Birch Park, Bottesford | Results |
| 28 Jun 2009 | | Everton Third XI v Upton cum Kexby | The Metcalfe Ground, Everton | Results |
| 28 Jun 2009 | | North Wheatley with Leverton Second XI v Barton Town Fourth XI | Playing Field, South Wheatley | Results |
| 05 Jul 2009 | | Bottesford Town Second XI v Barton Town Fourth XI | Birch Park, Bottesford | Results |
| 05 Jul 2009 | | Grimsby Town Development XI v Everton Third XI | Augusta Street, Grimsby | Results |
| 05 Jul 2009 | | Misterton Second XI v Upton cum Kexby | Marsh Lane, Misterton | Results |
| 12 Jul 2009 | | Bottesford Town Second XI v North Wheatley with Leverton Second XI | Birch Park, Bottesford | Results |
| 12 Jul 2009 | | Everton Third XI v Misterton Second XI | The Metcalfe Ground, Everton | Results |
| 12 Jul 2009 | | Grimsby Town Development XI v Upton cum Kexby | Augusta Street, Grimsby | Results |
| 19 Jul 2009 | | Barton Town Fourth XI v Misterton Second XI | Marsh Lane, Barton on Humber | Results |
| 31 Aug 2009 | | Everton Third XI v Barton Town Fourth XI | The Metcalfe Ground, Everton | Results |
| 19 Jul 2009 | | Everton Third XI v Bottesford Town Second XI | The Metcalfe Ground, Everton | Results |
| 19 Jul 2009 | | Grimsby Town Development XI v North Wheatley with Leverton Second XI | Augusta Street, Grimsby | Results |
| 26 Jul 2009 | | Misterton Second XI v Grimsby Town Development XI | Marsh Lane, Misterton | Results |
| 26 Jul 2009 | | North Wheatley with Leverton Second XI v Upton cum Kexby | Playing Field, South Wheatley | Results |
| 02 Aug 2009 | | Misterton Second XI v Everton Third XI | Marsh Lane, Misterton | Results |
| 02 Aug 2009 | | North Wheatley with Leverton Second XI v Bottesford Town Second XI | Playing Field, South Wheatley | Results |
| 02 Aug 2009 | | Upton cum Kexby v Grimsby Town Development XI | Upton cum Kexby Playing Field, Kexby | Results |
| 09 Aug 2009 | | Bottesford Town Second XI v Upton cum Kexby | Birch Park, Bottesford | Results |
| 09 Aug 2009 | | Everton Third XI v North Wheatley with Leverton Second XI | The Metcalfe Ground, Everton | Results |
| 09 Aug 2009 | | Grimsby Town Development XI v Barton Town Fourth XI | Augusta Street, Grimsby | Results |
| 16 Aug 2009 | | Barton Town Fourth XI v North Wheatley with Leverton Second XI | Marsh Lane, Barton on Humber | Results |
| 16 Aug 2009 | | Misterton Second XI v Bottesford Town Second XI | Marsh Lane, Misterton | Results |
| 16 Aug 2009 | | Upton cum Kexby v Everton Third XI | Upton cum Kexby Playing Field, Kexby | Results |
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