Past winners of the Punniest of Show portion of the O. Henry Pun-Off.

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

1995
1st – John Pollack