NSW CHS Champion Boys Schools
| Year | First | Second | Third |
|---|---|---|---|
| 1965 | Homebush Boys HS | Narwee Boys HS | |
| 1966 | Sydney Boys HS | Homebush Boys HS | Cleveland Street |
| 1967 | North Sydney Boys HS | ? | Homebush Boys HS |
| 1968 | Telopea Park HS | ||
| 1969 | (not known) | ||
| 1970 | South Grafton HS | Grafton HS | Homebush Boys HS |
| 1971 | Penrith HS | Homebush Boys HS | Grafton HS |
| 1972 | Sydney Boys HS | Penrith HS | Homebush Boys HS |
| 1973 | Penrith HS | ||
| 1974 | Penrith HS | Sydney Boys HS | South Grafton HS |
| 1975 | Sydney Boys HS | ||
| 1976 | Sydney Boys HS | ||
| 1977 | Sydney Boys HS | ||
| 1978 | Sydney Boys HS | ||
| 1979 | Taree HS | Sydney Boys HS | Nepean HS |
| 1980 | Nepean HS | Taree HS | Grafton HS Homebush Boys HS |
| 1981 | Taree HS | North Sydney Boys HS | Nepean HS Sydney Boys HS |
| 1982 | Sydney Boys HS | Taree HS | Homebush Boys HS Sydney Tech HS |
| 1983 | Sydney Boys HS | Taree HS | Nepean HS |
| 1984 | Nepean HS | Taree HS Maclean HS |
|
| 1985 | Maclean HS | Nepean HS | Sydney Boys HS |
| 1986 | Grafton HS | Maclean HS Nepean HS |
|
| 1987 | Sydney Boys HS | Nepean HS | Grafton HS |
| 1988 | Grafton HS | Sydney Boys HS | Maclean HS |
| 1989 | Sydney Boys HS | Grafton HS | Nepean HS |
| 1990 | Sydney Boys HS | Grafton HS | Maclean HS |
| 1991 | Sydney Boys HS | Murwillumbah HS | Grafton HS |
| 1992 | Sydney Boys HS | ||
| 1993 | Sydney Boys HS | North Sydney Boys HS | Maclean HS |
| 1994 | (not known) | ||
| 1995 | Sydney Boys HS | Maclean HS | Taree HS |
| 1996 | Maclean HS | Grafton HS South Grafton HS |
|
| 1997 | (not known) | ||
| 1998 | South Grafton HS | Taree HS | Maclean HS |
| 1999 | South Grafton HS | Maclean HS | Kirrawee HS |
| 2000 | South Grafton HS | Sydney Boys HS | Maclean HS |
| 2001 | South Grafton HS | Maclean HS | Grafton HS |
| 2002 | South Grafton HS | Taree HS | Maclean HS |
| 2003 | Sydney Boys HS | South Grafton HS | Maclean HS |
| 2004 | Sydney Boys HS | South Grafton HS | Grafton HS |
| 2005 | Sydney Boys HS | Maclean HS | South Grafton HS |
| 2006 | Sydney Boys HS | Grafton HS | South Grafton HS Maclean HS |
| 2007 | Sydney Boys HS | Maclean HS | Grafton HS |
| 2008 | Sydney Boys HS | Maclean HS | Jamison HS |
| 2009 | Championships cancelled due to flooding |
||
| 2010 | Sydney Boys HS | Maclean HS | Grafton HS |
| 2011 | Sydney Boys HS | Maclean HS | Merewether HS |
| 2012 | Championships cancelled due to flooding |
||
| 2013 | Sydney Boys HS | Grafton HS | South Grafton HS |
| 2014 | Sydney Boys HS | Merewether HS | Maitland Grossmann Concord HS |
| 2015 | Sydney Boys HS | Maitland Grossmann HS | Concord HS |
| 2016 | Sydney Boys HS | Maitland Grossmann HS | Concord HS South Grafton HS |
| 2017 | Grafton HS | Kingscliff HS | Maitland Grossmann HS |
| 2018 | Sydney Boys HS | Maitland Grossmann HS | Sydney Secondary College |
| 2019 | Sydney Boys HS | Sydney Secondary College | Maclean HS |
| 2020 | Sydney Boys HS | Northern Beaches Secondary | Sydney Secondary College |
| 2021 | Sydney Boys HS | Northern Beaches Secondary | Cammeraygal HS |
| 2022 | Northern Beaches Secondary | Sydney Boys High School | South Grafton High School |
| 2023 | Northern Beaches Secondary | Sydney Boys High School | Sydney Secondary College |