MASTERS MEN 40
1995
Outrigger Canoe Club
Tom Merrill
Mike Town
Tay Perry
Charles May
Kawika Grant
Bruce Ames
MASTERS MEN 50
1996
Kailua Canoe Club
Howard Keller
Pat Goldstein
Rem Mikus
Phil Schmidt
Bob Thurston
Gary Oakland
1997
Anuenue Canoe Club
Babe Bell
Mike Watson
Jerry Evansville
Sam Rodriguez
Henry Ho
Nappy Napoleon
MASTERS MEN 52
1998
Anuenue Canoe Club
Babe Bell
Peter Caldwell
Hardy Spoehr
Rockne Freitas
Jon Miki
Nappy Napoleon
MASTERS MEN 53
1999
Kailua Canoe Club
Howard Keller
Robert Thurston
Patrick Goldstein
Phillip Schmidt
Joseph Kaneakua
Bernabe Quitevis
2000
Kailua Canoe Club
Bob Thurston
Patrick Goldstein
Phil Schmidt
Hank Leandro
Howard Keller
Thomas Conner
MASTERS MEN 55
2001
Outrigger Canoe Club
Tay Perry
Roger Cundall
Chris McKenzie
Joe Dubiel
Glenn Perry
Bruce Ames
2002
Outrigger Canoe Club
Chris McKenzie
John Finney
Mike Clifford
Tay Perry
Roger Cundall
Walter Guild
2003
Kailua Canoe Club
Hank Leandro
Mike Watson
Paul Shaner
Pat Goldstein
Bob Thurston
Tom Conner
2004
Lanikai Canoe Club
Jerome Cox
Michael Gibson
George Medeiros
William Watson
Carl Woehrle
John Foti
2005
Lanikai Canoe Club
Jerome Cox
Michael Gibson
Bill Henderson
Jack Laufer
Tay Perry
Nahina Lee Loy
MASTERS MEN 60
2006
Lanikai Canoe Club
Fred Hemmings Jr.
George Medeiros
William Monahan
Tay Perry
Shaka Madali
William Watson
2007
Lanikai Canoe Club
Clinton Mathews
William Monahan
John Myrdal
Melvyn Chow
William Watson
Fred Hemmings Jr.
2008
Kailua Canoe Club
Howard Keller
Hank Leandro
Bill Lockyer
Robert Thurston
Gary Oakland
Heath Hemmings
2009
Keahiakahoe Canoe Club
Keith Kaleo
Glenn Higuchi
Hollywood Alcantara
Yama Yamasaki
Doug Aton
Gary Sword Murakami
2010
Anuenue Canoe Club
Robert Berghell
J Cappy Sheely
Jon Miki
Gaylord Wilcox
Samson Rodrigues
David Napoleon
MASTERS MEN 65
2011
Outrigger Canoe Club
Tay Perry
Henry Richmond
John Finney
Glenn Perry
Ron Hochuli
Jim Beaton
2012
Outrigger Canoe Club
Ronald Hochuli
Al Van Gieson
Tay Perry
Mark Buck
William Johnson
Glenn Perry
2013
Outrigger Canoe Club
Roger McNicoll
Glenn Perry
Allan Maddalena
William Mowat
William Johnson
Billy Lawson
2014
Outrigger Canoe Club
Mark Buck
Juvie Coito
Glenn Perry
William Mowat
William Johnson
Billy Lawson
2015
Waimanalo Canoe Club
Harold Akeo
Jeff Metzger
Boy Kalama
Dennis Sallas
Ted Ralston
Raymond Lii
MASTERS MEN 70
2016
Outrigger Canoe Club
Michael Clifford
Allan Maddalena
Ronald Hochuli
John Finney
Uli Klinke
Simeon Ke-Paloma
2017
Lanikai Canoe Club
Rob Milne
Steve Kux
Ron Seiple
Mike Gorza
Jeff Hunt
Scott Freitas
4:21.58
2018
Outrigger Canoe Club
Michael Durkin
John Finney
Ronald Hochuli
Uli Klinke
Kimbal Thompson
Jimmy Austin
4:18.37
2019
Outrigger Canoe Club
Kenny Bailey
Mark Buck
John Finney
Uli Klinke
David Shoji
Heinere Itchner
4:23.60
2020
Regatta cancelled due to COVID 19
2021
Regatta cancelled due to COVID 19
2022
Outrigger Canoe Club
John Finney
Uli Klinke
Richard Ray
Darryll Wong
Derrick Wong
Jimmy Austin
4:27.40