Race History

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Past Winners & Times

Past Winners and Times

Kanaka Ikaika Racing Association is Hawaii’s oldest organized kayak association. Each May, the world’s best surfski paddlers enter the ocean at Molokai’s Papohaku Roadstead to compete in the Molokai Challenge: A race to Oahu. Because of the large international field this race attracts it is considered the World Championship of Open Ocean Surfski and Solo Canoe Racing.

1976 was the first crossing by Dale “Doc” Adams in an ocean going kayak. His solo effort took him 7 hours and 30 minutes. Doc Adams called his crossing “the challenge of the day,” but it has since developed into the premier long-distance, open ocean, solo crossing in the world.

In 1977 Adams consulted Hawaiian linguist Pilahi Paki who described the effort as “Kanaka Ikaika,” which literally translated means:

Mankind’s respectful challenge of the great, mighty ocean.

Paki’s name for the crossing became the name of the paddling club.

1977 was the first official race, organized by newly formed Kanaka Ikaika Racing Association with Doc Adams at the helm.

The Molokai Challenge, originally named Kanaka Ikaika, is the ultimate Ironman and final test of paddling skill, endurance and knowledge of ocean surfing. It tests a paddler’s ability to maneuver against unpredictable weather conditions in the Kaiwi Channel.  The Kaiwi Channel, more often called the “Molokai Channel” is an expanse of ocean between the island of Molokai and Oahu. It is considered one of the roughest ocean channels in the world when Mother Nature is angry.

The start is off the west end of Molokai near Kaluakoi, and traditionally finishes 32 miles away in the Marina off Hawaii Kai.   In 2007 the race finished in Waikiki as a test to see if the extra 8 miles would be accepted by the paddlers.   There was no wind, 44 entrants pulled out, and the winning time was 5 hours and 20 minutes. The course returned to Hawaii Kai the following year and has not changed since.

Traditionally the Molokai Challenge was a solo invitational event for surfskis only. However, as the one person canoe (OC-1) emerged in the 1990s, Kanaka Ikaika embraced the new craft and had a combined event. However, in 2007 Kanaka Ikaika gave the race away, and within a few years, there was a dedicated OC-1 Molokai channel race and the Molokai Challenge was back to only the Surfski division.

2013 Kanaka Ikaika changed management and in 2014 the Molokai Challenge came back home. As Kanaka Ikaika is an organization that has grown to embrace all paddle disciplines, the new regime opened up again to OC-1s, as well as Prone Paddleboards and Stand Up Paddling. And in an effort to build and enhance Paddlesports, the 2015 Molokai Challenge will also allow relay divisions to participate.

The 2015 race is the 40th annual crossing, counting the 1976 solo effort by Doc. Adams.

  • 1976 ~ Doc. Adams paddled for 7 hours, 30 minutes in his first effort.
  • 1977 ~ Adams repeated the crossing with Dean Hayward, a marathon runner and coach at Kamehameha Schools, and Jorgen Hansen, a veteran international surfski paddler. Hayward finished first in 6 hours, 45 minutes.
  • 1978 ~ Kalai Handley of Kailua, Oahu, won the race and since that time no other male competitor from Hawaii has finished first in the surfski division.
  • 1979 ~ 18 Entrants Finished
    Paddlers made the crossing, including the first international competitor, Grant Kenny of Australia, who won the race in 5:37:05.
  • 1980 ~ Eve Anderson became the first female competitor and Chuck Bennett, a paraplegic, was the first physically challenged entrant. Grant Kenny repeats as winner
  • 1981 & 1982 ~ Grant Kenny wins again making a 4 year win streak
  • 1983 – 1984 ~ Enter Oscar Chalupski from South Africa who wins them both back to back!
  • 1985 ~ Tahitian Born Lesline Conner of Waimanalo won the female division in 5 hours 59 minutes for her first Molokai Challenge victory. Oscar wins his 3rd title.
  • 1986 ~ Oscar wins his 4th consecutive title.         Julie Leach beats Conner for the female division.
  • 1987 ~ Oscar surges to the all time high 5 victories. Lesline Connor takes back the female division.
  • 1988 ~ Oscar wins yet again. The race attracted 45 competitors from Australia, Hawaii and South Africa. Lore Bode from Hawaii wins the female division in 4 hours 44 minutes.
  • 1989 ~ 67 Entrants (44 Entrants Finished). Oscar Chalupsky wins again, posting his 7th straight victory with a time of 3:39:47, beating Greg Barton, American Olympic Gold Medalist.         Lesline Conner wins again in the female division.
  • 1990 ~ 58 Entrants Finished. Bronze Medallist Grand Kenny made a successful return to the winners circle, crossing the channel in 3:44:45 for his fifth win.  Lesline Conner won the race for her fourth time.
  • 1991 ~ Guy Leech wins the men’s for his first time and Jane Hall from Australia claims the win for the female division.
  • 1992 ~ Enter the era of Dean Gardiner who wins his first Molokai Challenge, with Jane Hall a repeat in the women’s division.
  • 1993 ~ Three time women’s winner, Jane Hall, from Sydney, Australia, set a new women’s record in a time of 4:14:23.  Australia’s Dean Gardiner won the kayak race for the second time and Pat Erwin of Kailua, Oahu won the solo canoe race in a time of 4:23:24.
  • 1994 ~ 74 Entrants Finished. The men’s and women’s surfski times were smashed.  Gardiner won again in 3:24:08 and Hawaii’s Kelly Fey posts her first win and broke Hall’s record with a time of 4:12:34.
  • 1995 ~ After battling one another across the Channel, brothers Oscar and Herman Chalupsky conferred shortly before the finish and decided to cross together.  A tie was declared as the two held onto one another’s surfski to cross the line.  Kelly Fey kept the women’s title and Kauai’s Steve Cole won the outrigger canoe division.
  • 1996 ~ Dean Gardiner led the kayak competition, winning his fourth race in five years with a time of 3:38:27. Followed by fellow Aussies Brad Kane and Martin Kenny, second and third place respectively, the Australian team easily captured the international team title.  Nalu Kukea, son of the late Kala Kukea, was the first Hawaii finisher and 4th overall.  Kelly Fey won again in the women’s Surfski.
  • In the solo canoe division, Mark Rigg triumphed in his first solo crossing with a time of 4:17:35, beating out 1994 winner Pat Erwin (4:25:15).  In the women’s open division, Sonia Lambert and Loretta Toth became the first women ever to cross the Kaiwi Channel in a solo canoe. Lambert won the race with a time of (5:30:35)
  • 1997 ~ Three-peat / four new records ~ Dean Gardiner continued his winning streak, finishing in a time of (3:21:26) Kelly Fey held onto her title with a time of( 4:02:47), as did solo canoeist Mark Rigg with a time of 4:14:52. In her first solo Molokai crossing, Donna Kahakui captured first place and a new record (5:16:29)
  • 1998 ~ Dean Gardiner repeated his 1997 men’s kayak victory in a time of 3:27:15, edging out Nalu Kukea who finished less than a minute later with a time of 3:28:09.  Gardiner was also part of the first place international team competition, a race-within-a-race, along with Australian team mates Martin Kenny and Brad Kane. Kelly Fey posts her 5th consecutive victory. The solo canoe battle between Mark Rigg and John Foti continued throughout the crossing of the Channel, with Rigg finishing first for the third consecutive year with a new record at that time, of 4:06:22, just one minute, two seconds ahead of John Foti (4:07:24). Kelly Fey continued her reign as the first female kayaker to cross, with a time of 4:09:53, followed by Nicole Montel of Tahiti with a time of 4:21:05.  In her first solo canoe crossing, Cheryl Villegas from the Big Island of Hawaii captured the first place women’s solo canoe title with a time of 5:21:10.  Last year’s champion, Donna Kahakui, finished second in 5:31:08.
  • 1999 ~ 99 Entrants Finished. Once again, Dean Gardiner continued his winning streak finishing with a time of 3:37:05 while 18 year old Karel Tresnak Jr. had a six minute lead on Mark Rigg in the OC-1 division with a time of 4:17:05.
  • 2000 ~ 77 Entrants Finished. Oscar Chalupsky came across the finish line with a time of 3:21:48. Karel Tresnak Jr. repeated his second win with a time of 3:49:19
  • 2001 ~ 75 Entrants Finished. Dean Gardiner edged out Lewis Laughlin in less than two minutes with a time of 3:35:57. Karel Tresnak Jr. did it again in the OC-1 by winning his third consecutive win with a time of 3:52:09. Mike Judd was close behind with a time of 3:54:35.
  • 2002 ~ 79 Entrants Finished. Australia takes first, second and third place. Dean Gardiner of Australia did it again with a better time than last year of 3:24:52. Martin Kenny of Australia was behind him for a second place finish of 3:27:24. Grant Kenny was right behind his Brother for a third place finish of 3:30:27. In the OC-1 Kai Bartlett had a great run at 3:42:37 while Mike Judd came in 2nd at 3:47:09. Kealii Paiaina took third with a 3:51:45.
  • 2003 ~ 81 Entrants Finished. Oscar Chalupsky returns for a showdown against Gardiner and came in first place with a time of 3:28:33. Karel Tresnak Jr. is back with a first place OC-1 win of 3:51:32 just ahead of Kai Bartlett with a second place finish of 3:52:57. Mike Judd came in with the third place finish of 3:56:51.
  • 2004 ~ 100 Entrants Finished Herman Chalupsky is the first Surfski to cross the finish line with a time of 3:48:40, Dave Kissane came in second with a 3:55:16 and Oscar Chalupsky third with a 3:58:10 OC-1 Karel Tresnak Jr. was back in play with a first place time of 4:11:15 with Mike Judd taking second with a 4:13:32 and a young Danny Ching with a third place finish of 4:22:23.
  • 2005 ~ 115 Entrants Finished. Oscar Chalupsky takes first place in the Surfski again with a time of 3:28:38. Nathan Baggaley comes in second place with a great time of 3:30:52 and Dean Gardiner takes a close third with a 3:31:45 OC-1 Kai Bartlett comes in first place with a time of 3:52:37. Mike Judd takes second with a 3:57:45 and in third place is Manny Kulukulualani with a 3:59:13.
  • 2006 ~ Clint Pretorius won in 3:22:14.
  • 2007 ~ 92 Entrants Finished. 44 DNF. New finish in Waikiki. Lewis Laughlin won in 5:20:06. Hank McGregor was second
  • 2008 ~ 119 Entrants Finished Lewis Laughlin won in 3:40:26. Hank McGregor was second
  • 2009 ~ 81 Entrants Finished. Hank McGregor won in 3:54:39. Tim Jacobs was second
  • 2010 ~ 52 Entrants Finished. Clint Robinson won in 3:23:02. Dean Gardiner was second
  • 2011 ~ Clint Robinson won in 3:51:58. Thomas Schilperoo was second
  • 2012 ~ 65 Entrants Finished. Oscar Chalupski won in 3:24:07. Clint Robinson was second
  • 2013 ~ Clint Robinson won
  • 2014 ~ Kanaka Ikaika takes back Molokai after a 7 year hiatus. 77 paddlers entered. Hank McGregor won in 3:35:17, only 33 seconds ahead of defending champ Clint Robinson. Rachel Clarke won the female division in 4:33:02
  • 2015 ~ Cory Hill breaks into the winner circle upstaging Clint Robinson by a minute and a half. Hank McGregor finishes 3rd. Only female paddlers in the race were OC-1. Mary Smolenski wins the solo.
  • 2016 ~ Hank McGregor wins his 3rd Molokai Challenge title at 3:45:34, Sean Rice was second.  Elizabeth Pluimers wins the women’s division in 4:18:33.  Kaihe Chong wins his 2nd OC-1 title.
  • 2017 ~ Sean Rice wins his 1st Molokai Challenge title. Hank McGregor is runner up.  Rachel Clark wins the women’s division for her 2nd  Kainoa Tanoai wins the OC-1.  There were no women solo OC-1.
  • 2018 ~ Cory Hill wins his second title in record time of 3:15:09 while Hayley Nixon from South Africa wins her first Molokai Challenge, also breaking the record at 3:52:32. Kainoa Tanoai successfully defends his OC-1 title with Andrea Moller winning her 1st OC-1 Molokai Victory.
  • 2019 ~ was the year of all record breaking years. Hank McGregor wins his 5th title with a new record of 3:11:17 and Jordan Mercer won her first title with a new record of 3:47:22.  The OC-1 champions also broke Kanaka Ikaika records: Tristan Kahookele Santos won his first title in 3:36:22, and Lauren Spalding won her 9th title, including the PAA Kaiwi Channel races in 4:10:12.  Plus Lauren has won the ski race 3 times in the past.
  • 2020, 2021, 2022 ~ COVID 19. No race.
  • 2023 ~