The overall winners of the Waikiki Roughwater Swim on Oahu in Hawaii was the model for the swim leg of the Hawaii Ironman. Its winners include some very impressive ocean swimmers including legendary Olympic gold medalist sprinter Jim Montgomery (1985) and 12-year-old phenomenon Kathy Shipman (1972) who finished fifth overall. The ageless Alex Kostich not only won the 1994, but also 12 years later amid an even more competitive field in 2006.

Paul Stader, Kaili Chun, Nadai Takai, and Luane Rowe had streaks of brilliance when they won races in consecutive years.

Competition and a keen sense of navigation have always played a part in determining the victors, especially in the surf towards the finish and over the coral reef and across the sand at the finish. In 1991 the top 3 finishers Bobby Patten, David Lundberg, and Rick Heltzel finished within 4 seconds of one another. In 1992, Karen Burton and Shelley Taylor-Smith scrambled up the beach together after going stroke-for-stroke for the entire distance.

All-time winners of the Waikiki Roughwater Swim:
1970 Marc Finley (55:23) and Marjorie Phillips (1:26:31)
1971 Jonathan Ezer (41:09) and Liz Hogan (46:20)
1972 Sam Chessler (43:49) and Kathy Shipman (46:49)
1973 Les Wulk (47:57) and Nancy Ivy (49:15)
1974 Brett Phillips (50:04) and Nalani Guyer (56:37)
1975 Brett Phillips (59:05) and Julia Francisco (54:00)
1976 Paul Stader (46:23) and Kaili Chun (47:47)
1977 Paul Stader (51:48) and Kaili Chun (56:18)
1978 Paul Stader (51:14) and Kaili Chun (55:32)
1979 Brett Phillips (48:02) and Kaili Chun (50:51)
1980 Paul Stader (49:43) and Kaili Chun (51:08)
1981 Joseph Lileikis (50:52) and Kaili Chun (56:33)
1982 Joseph Lileikis (48:18) and Kaili Chun (51:34)
1983 Max Metzker (49:48) and Amy White (59:02)
1984 Rick Heltzel (43:47) and Kaili Chun (46:58)
1985 James Montgomery (1:00:29) and Jane Cooper (1:16:18)
1986 Jeff Stiling (54:15) and Nadine Takai (59:19)
1987 Christopher Moore (51:13) and Nadine Takai (55:49)
1988 Paul Asmuth (45:32 and Nadine Takai (46:55)
1989 Darren Turner (50:13) and Bronwyn Burns (54:19)
1990 Christopher Moore (50:16) and Ann Peters (58:19)
1991 Bobby Patten (45:42) and Lisa Johns (46:00)
1992 Daniel McLellan (55:09) and Karen Burton (55:57)
1993 Darren Turner (42:38) and Lisa Hazen (47:39)
1994 Alex Kostich (53:08) and Kari Lydersen (57:46)
1995 Daniel McLellan (42:13) and Lisa Hazen (45:33)
1996 Malcolm Allen (51:110 and Stacey Gartrell (56:58)
1997 Malcolm Allen (48:20) and Stacey Gartrell (48:44)
1998 Dean Mercer (50:58) and Kasey Giteau (57:24)
1999 Malcolm Allen (49:55) and Jodi Jackson (55:54)
2000 John Flanagan (48:58) and McCall Dorr (56:58)
2001 John Flanagan (52:40) and Trudee Hutchinson (57:31)
2002 Alex Kostich (43:46) and Dawn Heckman (47:06)
2003 Grant Cleland (1:04:25) and Trudee Hutchinson (1:17:16)
2004 Noa Sakamoto (49:26) and Cassie Hunt 56:37)
2005 Event Cancelled
2006 Alex Kostich (45:25) and Claudia Bars (52:40)
2007 Noa Sakamoto (43:37) and Emma Berry (53:24)
2008 Trent Grimsey (47:59) and Luane Rowe (55:01)
2009 Trent Grimsey (42:20) and Luane Rowe (47:21)
2010 Travis Nederpelt (45:40) and Luane Rowe (51:18)
2011 George O’Brien (43:40 and Luane Rowe (49:06)
2012 Rhys Mainstone (47:29) and Becca Mann (50:38)
2013 Rhys Mainstone (48:10) and Miranda Bell (53:05)
2014 Simon Huitenga (45:36) and Becca Mann (51:22)

and Becca Mann (51:22)

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