| Team | Individual | ||||||
| 1973 | St. Raymond's | 57 | Ibracken | Cardinal Hayes | 8:58 | ||
| 1974 | Mt. St. Michael | 41 | V. Mutarelli | Mt. St. Michael | 8:27 | MR | |
| 1975 | Mt. St. Michael | 41 | McCarthy | 8:40 | |||
| 1976 | Mt. St. Michael | 38 | Jennings | Mt. St. Michael | 9:25 | ||
| 1977 | St. Raymond's | 30 | Smith | Msgr. Scanlon | 9:40 | ||
| 1978 | Mt. St. Michael | 39 | Dow | St. Raymond's | 8:57 | ||
| 1979 | St. Raymond's | 36 | I. Mitchell | Mt. St. Michael | 8:58 | ||
| 1989 | All Hallows | 26 | R. Mendez | Fordham Prep | 9:44 | ||
| 1990 | Fordham Prep | 24 | D. Reyes | St. Raymond's | 9:24 | ||
| 1991 | Fordham Prep | 36 | D. Graham | Mt. St. Michael | 9:14 | ||
| 1992 | Fordham Prep | 31 | D. Santillan | Mt. St. Michael | 9:33 | ||
| 1993 | Fordham Prep | 17 | T. Young | Fordham Prep | 9:02 | ||
| 1994 | Fordham Prep | 16 | R. Cassidy | Fordham Prep | 9:54 | ||
| 1995 | St. Raymond's | 29 | L. London | St. Raymond's | 9:21 | ||
| 1996 | Fordham Prep | 28 | K. Campbell | Mt. St. Michael | 9:23 | ||
| 1997 | Fordham Prep | 25 | T. Lynch | Fordham Prep | 9:30 | ||
| 1998 | Fordham Prep | 21 | J. Fitzsimons | Fordham Prep | 9:33.4 | ||
| 1999 | Fordham Prep | 15 | M. Matero | Fordham Prep | 9:47.7 | ||
| 2000 | Fordham Prep | 27 | J. Rodriguez | St. Raymond's | 9:40.0 | ||
| 2001 | Fordham Prep | 20 | G. Penasso | Mt. St. Michael | 9:37.9 | ||
| 2002 | Fordham Prep | 23 | T. Egan | Fordham Prep | 9:40.5 | ||
| 2003 | Mt. St. Michael | 35 | T. Neilis | Mt. St. Michael | 9:25.0 | ||
| 2004 | Fordham Prep | 22 | M. Lamb | Cardinal Hayes | 9:36.6 | ||
| 2005 | Fordham Prep | 17 | P. O'Connell | Fordham Prep | 9:13.4 | ||