| Season: 2008-2009 | Holder: ESTON & NORMANBY DYNAMO F.C. First |
about this competition.
Past winners (1980-2008)
- 1982-83 Guisborough Quoit Club
- 1983-84 Thornaby National Reserve
- 1984-85 Thornaby National Reserve
- 1985-86 St Peters Athletic
- 1986-87 Mars Inn
- 1987-88 Park Hotel
- 1988-89 Redcar WMC
- 1989-90 Redcar WMC
- 1990-91 Millers Yard
- 1991-92 West Pier Scarborough
- 1992-93 Normanby Hall CC
- 1993-94 Robert Thomsons Thirsk
- 1994-95 Normanby Hotel
- 1995-96 Masham
- 1996-97 Robert Thompsons Thirsk
- 1997-98 Normanby Hotel
- 1998-99 Redcar Dynamo
- 1999-00 Osmotherly Rangers
- 2000-01 Normanby Hotel
- 2001-02 West Pier Scarborough
- 2002-03 Hemlington SC
- 2003-04 Middlebeck
- 2004-05 Erimus
- 2005-06 Middlebeck
- 2006-07 Trafalgar
- 2007-08 Eston & Normanby Dynamo
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