Past winners of the Punslingers portion of the O. Henry Pun-Off.

2022 (In-person, but held in October)
1st – Dav Wallace
2nd – Jerry Yan
3rd – Arun Dubray and Toby Miceli-Gwiazdowski

2021 (virtual)
1st – Nikolai Vanya
2nd – Arun Debray
3rd – Manny Marshall

2020 (virtual)
1st – Dav Wallace
2nd – Arun Debray
3rd – David Wade and Max Parke

2019
1st – Allison Fisher
2nd – Arun Debray
3rd – Jerry Yan and Michael Maskin

2018
1st – Jerzy Gwiazdowski
2nd – Max Parke
3rd – Allison Fisher and Jerry Yan

2017
1st – Jerzy Gwiazdowski
2nd – Dav Wallace
3rd – Matt Pollack and Randall Kirsch

2016
1st – Ben Ziek
2nd – Toby Micel-Gwiazdowski
3rd (tie) – Jerry Yan and Tim Donnelly

2015
1st – Ben Ziek
2nd – Jerzy Gwiazdowski
3rd (tie) – Matt Pollock and Brian Agler

2014
1st – Matt Pollock
2nd – Ben Ziek
3rd (tie) – Dav Wallace and Chad Wellington

2013
1st – Ben Ziek
2nd – Matt Pollock
3rd (tie) – Alex Petri and Dav Wallace

2012
1st – Dav Wallace
2nd – Ben Ziek
3rd (tie) – Andy Balinsky and Matt Pollock

2011
1st – Ben Ziek
2nd – Dav Wallace
3rd – Jason Epstein

2010
1st – Ben Ziek
2nd – Jason Epstein
3rd (tie) – Matt Pollock and Jack White

2009
1st – Matt Pollock
2nd – Ben Ziek
3rd – Steve Nagle

2008
1st – Valerie Ward
2nd – Matt Pollock
3rd – Satya Manz

2007
1st – Arthur Simone
2nd – Carmen Petrick
3rd – David Gugenheim

2006
1st – David Gugenheim
2nd – Andy Balinksy
3rd – Arthur Simone

2005
1st – Brian Oakley
2nd – Gregory Chandler
3rd (tie) – David Gugenheim and Alex Ramirez

2004
1st – Alex Ramirez

2003
1st – Brian Snider
2nd – ?
3rd – Steve Nagle

2002
1st – Alex Ramirez

2001
1st – Alex Ramirez

2000
1st – Alex Ramirez

1999
1st – Alex Ramirez

1998
1st – Paul Mott

1997
1st – Steve Brooks

1995
1st – John Pollack

1994
1st – Steve Brooks

1991
1st – Lee Jackson