Challenge Series
Portsmouth Sailing Club One Design Challenge Cup Presented By A. Macpherson 1923 Won Outright By Harry Feltham And Presented By Mrs Ivy Male To Tudor Sailing Club
Handicap series of 3 races (with 1 discard) open to all. Sailed in conjunction with the Gould Series.
| Year | Helm | Crew | Boat / Class |
|---|---|---|---|
| 1921 | H Feltham | - | - |
| 1922 | H Feltham | - | - |
| 1923 | H Feltham | - | - |
| 1972 | F George | 1 off H'cap race for the Challenge Shield | Mini sail |
| 1976 | J Dakin | - | - |
| 1977 | - | - | - |
| 1978 | G Jones | - | - |
| 1979 | Middleditch | - | - |
| 1980 | T Small B | - | - |
| 1981 | Holden | - | - |
| 1982 | J Langham-Brown | - | - |
| 1983 | P Reeves | - | - |
| 1984 | S Pipes | - | Laser |
| 1985 | S Pipes | Single Race | Europe |
| 1986 | T Small | - | Laser |
| 1987 | B Smith | - | Finn |
| 1988 | T Small | - | Laser |
| 1989 | T Small | - | Laser |
| 1990 | J Powell | - | Fireball |
| 1991 | I Farr | - | Laser |
| 1992 | R Collins | S Coomber | Fireball |
| 1993 | J Powell | R Powell | Fireball |
| 1994 | J Powell | N Cosh | Fireball |
| 1995 | R Allen | - | Europe |
| 1996 | T Small | - | Laser |
| 1997 | T Small | - | Laser |
| 1998 | A Powell | - | Laser |
| 1999 | T Small | - | Laser |
| 2000 | Not Sailed | - | - |
| 2001 | T Small | - | Laser |
| 2002 | T Small | Laser | |
| 2003 | Terry Small | - | Laser |
| 2004 | A Small | T Small | Wayfarer |
| 2005 | M Webb | - | RS 600 |
| 2006 | I Farr | Laser | |
| 2007 | C Ayres | L Rich | Buzz |
| 2008 | Neil Boyce | Anita Boyce | Wayfarer |
| 2009 | James Bottoms | Anne Hulbert | Graduate |
| 2010 | Max Matthews | Guy Rivington | RS Feva XL |
| 2011 | Brian McGill | - | Laser Radial |
| 2012 | Steve O'Connor | - | Laser |
| 2013 | Neil Boyce | Laser | |
| 2015 | Richard Gardiner | Laser Radial | |
| 2016 | Steve Carr | - | Laser Radial |
| 2017 | Terry Small | Sandie Parker | Wayfarer |
| 2018 | Alan Saunders | LIGHTNING 368 | |
| 2019 | Emily Calkin | n/a | Laser 4.7 |
| 2021 | Neil Boyce | n/a | Laser Radial |
| 2022 | Ian Barrett | n/a | Laser |
| 2023 | Terry Small | Alison Small | Wayfarer |