The Pioneer Cup was presented by International Paints Ltd. in 1963 for the winner of the first race at the first ever Mirror Open at Wraysbury SC. Subsequently it is awarded to the 2nd Helm overall at the National Championships. So holders should be the 2nd place helm in the list of Past National Champions.
Here are some photographs of past winners
| Year | Held by | Note |
| 2022 | Chris & Adriana Balding | |
| 2021 | Simon Hiscocks & Josephine Rist-Heppell | |
| 2019 | Chris & Alex Balding | |
| 2018 | Edward Coady & Abi Cowley | |
| 2017 | Simon & Tyson Barwood (AUS) | Held by Martin Egan |
| 2016 | Melissa Heppell & Amelie Hiscocks | |
| 2015 | Angus & Florence Hemmings | |
| 2014 | Dave & Ed Coady | |
| 2013 | Reg Grayson & George Stainforth | |
| 2012 | Milly & Nick Pugh | |
| 2011 | Edward & Bethany Grey | |
| 2010 | Edward & Bethany Grey | |
| 2009 | Tom Lovesey & Milly Pugh | |
| 2007 | Ross Kerney & Katy Jones | |
| 2006 | Peter Gray & Anna Mackenzie | |
| 2005 | Anna Mackenzie & Holly Scott | |
| 2004 | Robert Struckett & Tom Hodkinson | |
| 2003 | Max Capener & Katy Jones | |
| 2002 | Stuart Bithell & Holly Scott | |
| 2001 | Alex Kaiser & John Vaughan (IRL) | |
| 2000 | Howard & Josh Tear | |
| 1999 | Guy & Ben Wilkins | |
| 1998 | Ian & Fay Capener | |
| 1997 | M McCarthy & Jack de Wolf | |
| 1996 | Philip Goodwin & Toby Heppell | |
| 1995 | Philip Goodwin & Toby Heppell | |
| 1994 | Steve Nicholson & Graham Vials | |
| 1993 | Ben Dutton & Alex Brereton | |
| 1992 | Luke Turnbull & Gillian Toman | |
| 1991 | J.D. & J.J. Gebhard | |
| 1990 | Mark Chadwick | |
| 1989 | Mark Chadwick & Leigh Smale | |
| 1988 | Peter Harper & Neil Hapgood | |
| 1987 | Guy & Teresa Wilkins | |
| 1986 | Guy & Teresa Wilkins | |
| 1985 | Dave Sherwin | |
| 1984 | Dave Sherwin | |
| 1983 | Dave Sherwin | |
| 1982 | Dave Sherwin | |
| 1981 | Mark Sherwin | |
| 1980 | Graham Castle | |
| 1979 | G. Owen | |
| 1978 | P Robinson | |
| 1976 | Harry & J Prangnell | |
| 1975 | Peter Barnes | |
| 1974 | Richard E. Dalby | |
| 1973 | Richard E. Dalby | |
| 1972 | Peter Barnes | |
| 1971 | Roy Partridge | |
| 1970 | John Taylor | |
| 1969 | John Taylor | |
| 1968 | F. Apthorpe | |
| 1967 | Roy Partridge | |
| 1966 | R. Gibson | |
| 1965 | F.W.T. Apthorpe | |
| 1964 | D. Wines | |
| 1963 | John & Ella Taylor | Wraysbury SC Mirror open |
