NYSFL Humorous Top 3 Finalists
| Year | Champion | Runner-Up | Third Place |
| 2003 | Jaclyn Silvestri, Syosset | Joseph Lento, Msgr. Farrell | Evan Faber, Bronx HS of Science |
| 2002 | Matt Sherbach, Chaminade | Dan Kessler, Hendrick Hudson | Jaclyn Silvestri, Syosset |
| 2001 | Matt Sherbach, Chaminade | Susan Liu, Stuyvesant | Johnathan Judge-Russo, Regis |
| 2000 | Chris LoBaito, Regis | Travis Benvenuti, Cold Spring Harbor | Dave Byrnes, Regis |
| 1999 | Chirag Badlani, Cold Spring Harbor | Michael Federico, Msgr. Farrell | Sasha Andreev, Stuyvesant |
| 1998 | Nikkole Baksh, Loyola School | Michael Littner, Bronx HS of Science | Fattaah Dihaan, Canisius |
| 1997 | John Sudol, Iona Prep | Billy Wheelan, Regis | Nikkole Baksh, Loyola School |
| 1996 | Evan Burnstein, Roslyn | Peter Collins, Webster | Anita Konka, Stuyvesant |
| 1995 | Ken Lin, Syosset | Jamil Ellis, Stuyvesant | Frank Todaro, Chaminade |
| 1994 | Matthew O'Brien, Stuyvesant | Eric Plosky, Syosset | Eric Paley, Roslyn |
| 1993 | Josh Schanker, Syosset | Eric Paley, Roslyn | Nancy Jacobs, Hendrick Hudson |
| 1992 | Jodi Zuckerman, Syosset | Peter Cumbo, Canisius | Kate George, Loyola |
| 1991 | Daren Firestone, Collegiate | Anthony Torre, Moore Catholic | Heather Finn, St. Joseph Hill |
| 1990 | Alexa O'Brien, Loyola | Diana Sulimovici, Stuyvesant | Michael Fanuele, Chaminade |
| 1989 | Diana Sulimovici, Stuyvesant | Heather Finn, St. Joseh Hill Academy | John Socas, Loyola |
| 1988 | Alexander Serban, Bronx HS of Science | Jono Mainelli, Bronx Science | Paul Angelilli, Iona |
| 1987 | Thomas Beck, Chaminade | John McGreal, Regis | Michael Zivyak, Syosset |
| 1986 | Alexa Eldred, Stuyvesant | Paul Leishman, Regis | Michael Zivyak, Syosset |
| 1985 | Federica Dussi, The Mary Louis Academy | Michael Gates, Bishop Kearney (Rochester) | Robert Kaplan, Syosset |
| 1984 | Brendan O'Meara, Bronx, Science | Peter Taback, Syosset | Joseph Hage, Xaverian |
| 1983 | Esther Schrader, Hendrick Hudson | Joseph Hage, Xaverian | Peter Cervoni, Iona |
| 1982 | Kevin Saulnier, St. Raymond | Stephen Tepper, Syosset | Peter Taback, Syosset |