| 2008 | Hayden Roulston (NZl) The Southland Times-Trek |
| 2007 | Hayden Roulston (NZl) Trek Zookeepers Cafe |
| 2006 | Hayden Roulston (NZl) Cycle Surgery |
| 2005 | Gordon McCauley (NZl) Trek/Zookeepers Cafe |
| 2004 | John Lieswyn (USA) The Southland Times |
| 2003 | Scott Guyton (NZl) The Southland Times |
| 2002 | John Lieswyn (USA) Winton's Middle Pub |
| 2001 | Karl Moore (NZl) Southroads |
| 2000 | Glen Mitchell |
| 1999 | Graeme Miller |
| 1998 | Scott Guyton |
| 1997 | Graeme Miller |
| 1996 | Gordon McCauley |
| 1995 | Brian Fowler |
| 1994 | Doug Bath |
| 1993 | Landrey Burt |
| 1992 | Brian Fowler |
| 1991 | Stuart Lowe |
| 1990 | Brian Fowler |
| 1989 | Brian Fowler |
| 1988 | Brian Fowler |
| 1987 | Brian Fowler |
| 1986 | Brian Fowler |
| 1985 | Brian Fowler |
| 1984 | Jack Swart |
| 1983 | Jack Swart |
| 1982 | Stephen Cox |
| 1981 | Stephen Cox |
| 1980 | Anthony Cuff |
| 1979 | Eric McKenzie |
| 1978 | Paul Jesson |
| 1977 | Wayne Perkinson |
| 1976 | Paul Jesson |
| 1975 | Chris Hogan |
| 1974 | Bruce Ramsey |
| 1973 | Michael Hughes |
| 1972 | Blair Stockwell |
| 1971 | John Dean |
| 1970 | David Gee |
| 1969 | Warwick Dalton |
| 1968 | Merv Davis |
| 1967 | Tino Tabak |
| 1966 | Tino Tabak |
| 1965 | Tino Tabak |
| 1964 | Malcolm Powell (Aus) |
| 1963 | Dick Johnstone |
| 1962 | Tony Walsh |
| 1961 | Warwick Dalton |
| 1960 | Gary Ulmer |
| 1959 | Warwick Dalton |
| 1957 | Tom Tindale |
| 1956 | Kelvin Hastie |
