Boys Champions
| Team Champion | Coach | Individual Champion | School | Time | |
| 1927 | St. John's | Vincent McArdle | Manhattan Prep | 13:36 | |
| 1928 | St James | George Eastment | John Ryan | Manhattan Prep | 14:08 |
| 1929 | St James | George Eastment | John Didie | St James | 12:24 |
| 1930 | St James | George Eastment | John Didie | St James | 12:41 |
| 1931 | Xavier | Paul Dee | Manhattan Prep | 12:39 | |
| 1932 | Manhattan Prep | Joseph Moclair | Manhattan Prep | 12:28 | |
| 1933 | Manhattan Prep | Joseph Moclair | Manhattan Prep | 12:14 | |
| 1934 | Brooklyn Prep | Bob Giegengack | Joseph Moclair | Manhattan Prep | 12:18 |
| 1935 | Brooklyn Prep | Bob Giegengack | Murtha Lawrence | Brooklyn Prep | 12:05 |
| 1936 | Bishop Loughlin | George Eastment | Harry Wilson | Bishop Loughlin | 12:56 |
| 1937 | Bishop Loughlin | George Eastment | John Winters | St Augustine | 12:11 |
| 1938 | Bishop Loughlin | George Eastment | Gerard Bennett | Bishop Loughlin | 11:59.3 |
| 1939 | DeLaSalle | Jim Walburton | Fred Araujo | DeLaSalle | 12:00 |
| 1940 | Bishop Loughlin | George Eastment | Charles Tietjen | Bishop Loughlin | 12:12.6 |
| 1941 | Bishop Loughlin | George Eastment | Lawrence Schmidt | Bishop Loughlin | 11:53.4 |
| 1942 | Bishop Loughlin | George Eastment | Arthur Sullivan | St Francis Prep | 11:59 |
| 1943 | Bishop Loughlin | George Eastment | James Nolan | Manhattan Prep | 12:26 |
| 1944 | Bishop Loughlin | George Eastment | Philip OConnell | Bishop Loughlin | 11:51 |
| 1945 | Bishop Loughlin | George Eastment | Philip OConnell | Bishop Loughlin | 11:55 |
| 1946 | Bishop Loughlin | William Miles | William Pates | St Augustine | 13:54 |
| 1947 | Bishop Loughlin | William Miles | Donald Anderson | Fordham Prep | 13:50.6 |
| 1948 | Bishop Loughlin | William Miles | William Berrgren | Fordham Prep | 14:02.4 |
| 1949 | Bishop Loughlin | William Miles | Albert Ray | Bishop Loughlin | 13:29.5 |
| 1950 | Bishop Loughlin | William Miles | Wilfred Stortz | Cardinal Hayes | 13:33.5 |
| 1951 | Cardinal Hayes | Howie Borck | James Daly | Chaminade | 13:01 |
| 1952 | Brooklyn Prep | Murths Lawernce | Edward McGuirk | Brooklyn Prep | 13:56 |
| 1953 | Bishop Loughlin | William Miles | Thomas Denny | Archbishop Stepinac | 13:42 |
| 1954 | Bishop Loughlin | William Miles | Roderick OSullivan | Rice | 13:35 |
| 1955 | Bishop Loughlin | William Miles | Roderick OSullivan | Rice | 13:52 |
| 1956 | St Francis Prep | James McHugh | George Verdisco | Archbishop Stepinac | 13:24.3 |
| 1957 | St Francis Prep | James McHugh | Tom Dempsey | Archbishop Stepinac | 13:26.0 |
| 1958 | Fordham Prep | Joe Fox | John Geraghty | Bishop Loughlin | 13:02.0 |
| 1959 | Fordham Prep | Joe Fox | Joseph McGovern | Fordham Prep | 13:25.7 |
| 1960 | Holy Cross | Br Walter Foley | Ed Duchini | Power Memorial | 13:12.2 |
| 1961 | Chaminade | Anthony Morelli | Ed Dean | Chaminade | 13:31.2 |
| 1962 | Archbishop Molloy | Frank Rienzo | Jim McDermott | Archbishop Molloy | 13:13.0 |
| 1963 | Archbishop Molloy | Frank Rienzo | Brian Kujawski | Archbishop Stepinac | 13:11.0 |
| 1964 | Archbishop Molloy | Frank Rienzo | Kevin Walsh | Power Memorial | 12:55.0 |
| 1965 | Power Memorial | John Mulligan | Frank Propopappas | Nazareth | 12:51.0 |
| 1966 | Power Memorial | John Mulligan | Bob Shanley | Sacred Heart | 12:51.4 |
| 1967 | Power Memorial | Br John Bielen | Denis Fikes | Rice | 12:50 |
| 1968 | St Agnes RVC | Larry Furnell | Denis Fikes | Rice | 12:42.4 |
| 1969 | Power Memorial | Br John Bielen | Denis Fikes | Rice | 12:25.7 |
| 1970 | Power Memorial | Br John Bielen | Brian Faraci | Fordham Prep | 12:40.2 |
| 1971 | Power Memorial | Br John Bielen | Kevin McCarey | Cathedral Prep | 12:25 |
| 1972 | Archbishop Molloy | Tony Perrone | Matt Centrowitz | Power Memorial | 12:38.2 |
| 1973 | Power Memorial | Br John Bielen | Gene McCarthy | All Hallows | 12:32.4 |
| 1974 | Power Memorial | Br John Bielen | Peter Crooke | St Anthonys | 12:48.5 |
| 1975 | Archbishop Molloy | Tony Perrone | Luis Ostolozaga | Bishop Loughlin | 12:29.8 |
| 1976 | St Anthonys | Don Buckley | John Gregorek | St Anthonys | 12:31.0 |
| 1977 | St Anthonys | Don Buckley | John Gregorek | St Anthonys | 12:34.8 |
| 1978 | St Anthonys | Don Buckley | Mike Cleary | Fordham Prep | 12:47.2 |
| 1979 | Msgr Farrell | George Kochman | Ed Healy | Msgr Farrell | 12:32.5 |
| 1980 | St Anthonys | Don Buckley | Lloyd Gellineau | St John the Baptist | 12:38.1 |
| 1981 | Msgr Farrell | Marty Walsh | Kevin Farrell | Holy Trinity | 12:53.3 |
| 1982 | Chaminade | William Carriero | Joseph Boyce | Holy Trinity | 12:42.9 |
| 1983 | Chaminade | William Carriero | Tom Nohilly | McClancy | 12:55.1 |
| 1984 | Mt St Michael | Br Linus Carroll | Neil Donohue | Msgr Farrell | 12:48.3 |
| 1985 | Msgr Farrell | John Agnello | Frank Odeh | Holy Cross | 12:55.4 |
| 1986 | Chaminade | William Carriero | Dan Baldwin | St Anthonys | 13:30.5 |
| 1987 | St Anthonys | Tim Dearie | John Tutttle | Moore Catholic | 12:51.4 |
| 1988 | St Anthonys | Tim Dearie | Phil Hemery | Archbishop Molloy | 12:38.2 |
| 1989 | Chaminade | William Carriero | Kevin Murphy | Chaminade | 12:53 |
| 1990 | Bishop Ford | Louis Vazquez III | Mark Naso | St Anthonys | 13:00.9 |
| 1991 | St Anthonys | Tim Dearie | William Vespe | Archbishop Molloy | 12:55.0 |
| 1992 | St Anthonys | Tim Dearie | Rey Mendez | Fordham Prep | 13:02.2 |
| 1993 | St Anthonys | Kevin Johnson | Ryan Maxwell | Msgr Farrell | 12:58.3 |
| 1994 | Msgr Farrell | Bob Marano/Bob Minall | William Arnold | Bishop Ford | 12:48.8 |
| 1995 | Chaminade | William Carriero | Mike McKeever | Chaminade | 13:22.3 |
| 1996 | Chaminade | William Carriero | Mike McKeever | Chaminade | 13:18 |
| 1997 | Chaminade | William Carriero | Andy Rupert | Chaminade | 13:17 |
| 1998 | St Anthonys | Tony Toro | Rolando Ortiz | St Peters | 12:56 |
| 1999 | St Anthonys-38 | Dan McGrath | Molloy | 12:46.4 | |
| 2000 | Chaminade-27 | William Carriero | Charles Millioen | St. Anthonys | 12:48.0 |
| 2001 | Kellenberg 65 | Kevin Buckley | Dan Naughton | Kellenburg | 13:00.54 |
| 2002 | St. Anthonys 45 | Tony Toro | Dan Naughton | Kellenburg | 12:53.07 |
| 2003 | Chaminade 64 | William Carriero | Brian McCabe | Fordham Prep | 12:50.72 |
| 2004 | Chaminade 31 | William Carriero | Kevin McDermott | Chaminade | 12:56.32 |
| 2005 | St. Anthonys | Tony Toro | Dan Lewis | Farrell | 12:50.02 |
| 2006 | Chaminade 50 | William Carriero | Ryan McDermott | Chaminade | 12:48.46 |
| 2007 | Chaminade- 42 | William Carriero | Thomas Elnick | Kellenberg | 12:59.69 |
| 2008 | Chaminade 51 | William Carriero | Paul Gilhuley | Bishop Ford | 12:59.59 |
| 2009 | St. Anthonys 37 | Tim Dearie | Ken Walshak | St. Anthonys | 12:55.91 |
| 2010 | St Anthonys-59 | Tim Dearie | William Slattery | Chaminade | 12:53.88 |
| 2011 | St. Anthonys - 46 | Tim Dearie | Dan Galford | Msgr. Farrell | 12:46.27 |
| 2012 | St, Anthonys -31 | Tim Dearie | Dan Galford | Msgr. Farrell | 12:45.82 |
| 2013 | Chaminade 38 | Bill Carriero | Tom Slattery | Chaminade | 12:32.40 |
| 2014 | St. Anthonys-36 | Tim Dearie | Patrick Tucker | St. Anthony's | 12:24.09 |
| 2015 | St. Anthonys-42 | Tim Dearie | Conor Lundy | Fordham Prep | 12:31.9 |
| 2016 | Xavier-57 | Pat Dormer | Ryan Tierney | St. Peter's | 13:02.21 |
| 2017 | Xavier-35 | Pat Dormer | Mason Gatewood | St. Anthony's | 12:40.8 |
| 2018 | Archbishop Molloy-61 | Frank Gambino | Matthew Payamps | St. Anthony's | 12:49.8 |
| 2019 | Xavier-54 | Pat Dormer | Niall Ryan | Fordham Prep | 12:49.3 |