| 30 Apr 2016 | First Round | Scothern Second XI v Louth Third XI | Playing Field, Scothern | Results |
| 30 Apr 2016 | First Round | Normanby Park v Messingham Second XI | Normanby Park Estate, Scunthorpe | Results |
| 30 Apr 2016 | First Round | Brigg Town v Appleby Frodingham Second XI | Brocklesby Park, Grimsby | Results |
| 30 Apr 2016 | First Round | Marshalls v Morton | Marshalls Sports Field, Gainsborough | Results |
| 30 Apr 2016 | First Round | Holton-le-Clay Second XI v East Halton | Tetney Lane, Holton-le-Clay | Results |
| 30 Apr 2016 | First Round | Cherry Willingham Second XI v Caistor Second XI | Playing Fields, Cherry Willingham | Results |
| 30 Apr 2016 | First Round | Outcasts Second XI v Alkborough Second XI | Hirst Priory Park, Crowle | Results |
| 22 May 2016 | First Round | Broughton Second XI v Hartsholme Second XI | Recreation Ground, Broughton | Results |
| 30 Apr 2016 | First Round | Clee Town Laportes v Market Rasen Second XI | Clee Road, Grimsby | Results |
| 30 Apr 2016 | First Round | Haxey Second XI v Alford Second XI | Haxey Lane, Haxey | Results |
| 30 Apr 2016 | First Round | Barton Town Second XI v Nettleham Second XI | Marsh Lane, Barton on Humber | Results |
| 30 Apr 2016 | First Round | Grimsby Town Second XI v Keelby Second XI | Augusta Street, Grimsby | Results |
| 30 Apr 2016 | First Round | Hibaldstow v Old Lincolnians | Station Road, Hibaldstow | Results |
| 28 May 2016 | Second Round | Morton v Haxey Second XI | Morton School, Morton | Results |
| 28 May 2016 | Second Round | Scothern Second XI v Caistor Second XI | Playing Field, Scothern | Results |
| 28 May 2016 | Second Round | Appleby Frodingham Second XI v Old Lincolnians | Brumby Hall, Scunthorpe | Results |
| 28 May 2016 | Second Round | Grimsby Town Second XI v Clee Town Laportes | Augusta Street, Grimsby | Results |
| 28 May 2016 | Second Round | Scunthorpe Town Second XI v Cleethorpes Second XI | Heslam Park, Scunthorpe | Results |
| 28 May 2016 | Second Round | Nettleham Second XI v Holton-le-Clay Second XI | Mulsanne Park, Nettleham | Results |
| 28 May 2016 | Second Round | Lindum Second XI v Outcasts Second XI | Lindum Sports Club Ground, Lincoln | Results |
| 28 May 2016 | Second Round | Broughton Second XI v Messingham Second XI | Recreation Ground, Broughton | Results |
| 26 Jun 2016 | Quarter-Final | Grimsby Town Second XI v Nettleham Second XI | Augusta Street, Grimsby | Results |
| 26 Jun 2016 | Quarter-Final | Lindum Second XI v Cleethorpes Second XI | Lindum Sports Club Ground, Lincoln | Results |
| 26 Jun 2016 | Quarter-Final | Morton v Broughton Second XI | Morton School, Morton | Results |
| 26 Jun 2016 | Quarter-Final | Appleby Frodingham Second XI v Caistor Second XI | Brumby Hall, Scunthorpe | Results |
| 24 Jul 2016 | Semi-Final | Lindum Second XI v Appleby Frodingham Second XI | Lindum Sports Club Ground, Lincoln | Results |
| 24 Jul 2016 | Semi-Final | Morton v Nettleham Second XI | Morton School, Morton | Results |
| 14 Aug 2016 | Final | Lindum Second XI v Nettleham Second XI | West Halton Lane, Alkborough | Results |
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