Engraved as the 'Matchplay Challenge Cup', we do not know who presented the trophy or when it was first played for.
The hallmarks on the trophy indicate that it was manufactured in London in 1937.
Prior to 1961, the trophy was awarded twice each year, at the Spring and Autumn Meetings. The first mention of the trophy as the Matchplay Handicap Challenge Cup is seen in the 1978 results section of the 1979 RAFGS handbook. This was also the first occasion when the trophy was listed with the results of the RAFGS Championship Meeting.
The trophy is currently awarded to the winner of the handicap competition, played over 36 holes of medal play at the Championship Meeting.
Current holder - Matt Branowsky
Winners
| Year | Winner | Year | Winner | Year | Winner |
| 2024 | SR Johnson | 2025 | GW Varley | 2026 | M Branowsky |
| 2021 | J Corlett | 2022 | DB Marshall | 2023 | GW Varley |
| 2018 | KLH Huish | 2019 | J Corlett | 2020 | No competition |
| 2015 | RDL Lushington | 2016 | SD Butler | 2017 | G Ascroft |
| 2012 | J Pearce | 2013 | SD Butler | 2014 | DB Marshall |
| 2009 | JVT Marks | 2010 | GW Varley | 2011 | G Ascroft |
| 2006 | RJ Pearson | 2007 | TA Brady | 2008 | DHW Backhouse |
| 2003 | JVT Marks | 2004 | JVT Marks | 2005 | JVT Marks |
| 2000 | NCW Barker | 2001 | MJ Middlemist | 2002 | KJ Watson |
| 1997 | GF Stocks | 1998 | GH Cunnington | 1999 | J Jagger |
| 1994 | WC Parke | 1995 | BB Considine | 1996 | WC Parke |
| 1991 | GKN Lloyd | 1992 | GKN Lloyd | 1993 | J Jagger |
| 1988 | CJ Redhouse | 1989 | PD Cliff | 1990 | GF Stocks |
| 1985 | WC Parke | 1986 | TM Bulloch | 1987 | PM Edge |
| 1982 | TM Bulloch | 1983 | PM Edge | 1984 | JJ Baynes |
| 1979 | JF Smith | 1980 | DH Mitchell | 1981 | JT Jennings |
| 1976 | K Hinkley-Smith | 1977 | CD Knapp | 1978 | BL Gilbert |
| 1973 | DR West | 1974 | LF Pilliner | 1975 | A Halsall |
| 1970 | R Porter | 1971 | PJ Dean | 1972 | RFL Wood |
| 1967 | W Witworth | 1968 | R Lowe | 1969 | J Deary |
| 1964 | JW Taylor | 1965 | MO Sullivan | 1966 | H Armitage |
| 1961 | DF Birch | 1962 | GW Bonney | 1963 | JM Ledbury |
| 1959 | Autumn - DC Matheson | 1960 | Spring - JM Ledbury | 1960 | Autumn - JR Burns |
| 1958 | Spring - GKN Lloyd | 1958 | Autumn - J Ballard | 1959 | Spring - R Hunter |
| 1956 | Autumn - A Fisher | 1957 | Spring - DC Evans | 1957 | Autumn - WDE Martin |
| 1955 | Spring - P Verdon | 1955 | Autumn - DWP Thrower | 1956 | Spring - J Cook |
| 1953 | Autumn - BH Andrews | 1954 | Spring - WS Aitken | 1954 | Autumn - WS Aitken |
| 1952 | Spring - B Fullerton | 1952 | Autumn - B Fullerton | 1953 | Spring - LH Keen |
| 1950 | Autumn - AHM McColl | 1951 | Spring - RS Nicholl | 1951 | Autumn - TR Leatherdale |
| 1949 | Apring - FG Roberts | 1949 | Autumn - PWJ Dawes | 1950 | Spring - MH Rhodes |