The Winter Cup was presented by F. Hughes, Esq. & J. Pidgeon, Esq.
The winner shall be the competitor with the lowest nett aggregate of four cards returned in the six Winter Monthly Medal Rounds held during September-April inclusive. In the event of a tie the winner will be decided by the lowest round or rounds.
| Year | Winner |
| 2020-21 | Cancelled |
| 2019-20 | P. Bean |
| 2018-19 | K. Pirrie |
| 2017-18 | G. Billington |
| 2016-17 | R. Dellar |
| 2015-16 | J.W. Moorfield |
| 2014-15 | G. Smith |
| 2013-14 | G. Smith |
| 2012-13 | R.Thompson |
| 2011-12 | S. Miller |
| 2010-11 | S.A. Harrison |
| 2009-10 | D.C.Barrett |
| 2008-09 | R. Montford |
| 2007-08 | M. Blinkhorn |
| 2006-07 | M.C. Hassall |
| 2005-06 | M. Sharples |
| 2004-05 | P.A. Harrison |
| 2003-04 | R.S. Dellar |
| 2002-03 | M. Riley |
| 2001-02 | R.D. Bunting |
| 2000-01 | S. Fletcher |
| 1999-2000 | J. Doran |
| 1998-99 | J. Critchley |
| 1997-98 | - |
| 1996-97 | - |
| 1995-96 | W.M. Denton |
| 1994-95 | R. Shippam |
| 1993-94 | D.A. Fletcher |
| 1992-93 | J.P. Malley |
| 1991-92 | J.W. Moorfield |
| 1990-91 | A.S. Hickman |
| 1989-90 | J.B. Conway |
| 1988-89 | R. Coveney |
| 1987-88 | W.W. Bickett & R. Montford |
| 1986-87 | T. Kelly & J. Flynn |
| 1985-86 | R.A. Clarke & R. Coveney |
| 1984-85 | J.P. Malley & P. Speakman |
