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Editions of the Molokai Challenge

Information about editions of the Molokai Challenge in Hawaii.


NAME: 2023 Molokai Challenge
ALSO KNOWN AS: Shaw and Partners Molokai Challenge 2023
DATE: May 28, 2023 (Sunday)
START: Kaluakoi Beach, west end of Molokai Island
FINISH: Maunalua Beach Park, Hawaii Kai, Oahu Island
- Adult Solo: Surfski1 / OC1 / V1 / SUP / Prone /
- Adult Solo OC2: Surfski2 / OC2 /
- Junior Solo: Surfski1 / OC1 / V1 / SUP / Prone /
- Junior Solo OC2: Surfski2 / OC2 /
- Adult Relay: Surfski1 / OC1 / V1 / SUP / Prone /
- Adult Relay: Surfski2 / OC2 /
- Junior Relay: Surfski1 / OC1 / V1 / SUP / Prone /
- Junior Relay OC2: Surfski2 / OC2 /

2022 - event not held | hepaddler.news | Facebook Note |
2021 - not held due to COVID?

EDITION: 2020 Molokai Challenge (CANCELLED)
DATE: Scheduled for May 24, 2020


EDITION: 44th Molokai Challenge
ALSO KNOWN AS: Maui Jim Molokai Challenge 2019
DATE: May 26, 2019 (Sunday)
START: Kaluakoi Beach, West end of Maui
FINISH: Kona Brew Pub, Koko Maribna, Hawaii Kai
- kanakaikaika.com --> maui jim molokai challenge 2019
- kanakaikaika.com --> results 2019 --> race 11 results
- youtube --> highlights by shaw and partners

EDITION: 43rd Molokai Challenge
ALSO KNOWN AS: Maui Jim Molokai Challenge 2018
YEAR: 2018
RESOURCE: kanakaikaika.com --> results 2018 --> race 11 results
- Cory Hill wins his second title in record time of 3:15:09
- 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
- Andrea Moller winning her 1st OC-1 Molokai Victory.

EDITION: 42nd Molokai Challenge
ALSO KNOWN AS: Maui Jim Molokai Challenge 2017
YEAR: 2017
RESOURCE: kanakaikaika.com --> results 2017 --> race 10 rsults
- 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.

EDITION: 41st Molokai Challenge
ALSO KNOWN AS: Maui Jim Molokai Challenge 2016
YEAR: 2016
RESOURCE: kanakaikaika.com --> results 2016 --> race 10 results
- 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.

EDITION: 40th Molokai Challenge
ALSO KNOWN AS: Maui Jim Molokai Challenge 2015
YEAR: 2015
RESOURCE: kanakaikaika.com --> results 2015 --> race 10 reasults
- 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.

EDITION: 39th Molokai Challenge
ALSO KNOWN AS: Maui Jim Molokai Challenge 2014
YEAR: 2014
RESOURCE: kanakaikaika.com --> molookai 2014 results
- 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

EDITION: 38th Molokai Challenge
YEAR: 2013
- Clint Robinson won

EDITION: 37th Molokai Challenge
YEAR: 2012
- 65 Entrants Finished. Oscar Chalupski won in 3:24:07. Clint Robinson was second

EDITION: 36th Molokai Challenge
YEAR: 2011
- Clint Robinson won in 3:51:58. Thomas Schilperoo was second

EDITION: 35th Molokai Challenge
YEAR: 2010
- 52 Entrants Finished. Clint Robinson won in 3:23:02. Dean Gardiner was second


EDITION: 34th Molokai Challenge
YEAR: 2009
- 81 Entrants Finished. Hank McGregor won in 3:54:39. Tim Jacobs was second

EDITION: 33rd Molokai Challenge
YEAR: 2008
- 119 Entrants Finished Lewis Laughlin won in 3:40:26. Hank McGregor was second

EDITION: 32nd Molokai Challenge
YEAR: 2007
- 92 Entrants Finished. 44 DNF. New finish in Waikiki. Lewis Laughlin won in 5:20:06. Hank McGregor was second

EDITION: 31st Molokai Challenge
YEAR: 2006
- Clint Pretorius won in 3:22:14.

EDITION: 30th Molokai Challenge
YEAR: 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.

EDITION: 29th Molokai Challenge
YEAR: 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.

EDITION: 28th Molokai Challenge
YEAR: 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.

EDITION: 27th Molokai Challenge
YEAR: 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.

EDITION: 26th Molokai Challenge
YEAR: 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.

EDITION: 25th Molokai Challenge
YEAR: 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


EDITION: 24th Molokai Challenge
YEAR: 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.

EDITION: 23rr Molokai Challenge
YEAR: 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.

EDITION: 22nd Molokai Challenge
YEAR: 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)

EDITION: 21st Molokai Challenge
YEAR: 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)

EDITION: 20th Molokai Challenge
YEAR: 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.

EDITION: 19th Molokai Challenge
YEAR: 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.

EDITION: 18th Molokai Challenge
YEAR: 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.

EDITION: 17th Molokai Challenge
YEAR: 1992
- Enter the era of Dean Gardiner who wins his first Molokai Challenge, with Jane Hall a repeat in the women’s division.

EDITION: 16th Molokai Challenge
YEAR: 1991
- Guy Leech wins the men’s for his first time and Jane Hall from Australia claims the win for the female division.

EDITION: 15th Molokai Challenge
YEAR: 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.


EDITION: 14th Molokai Challenge
YEAR: 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.

EDITION: 13th Molokai Challenge
YEAR: 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.

EDITION: 12th Molokai Challenge
YEAR: 1987
- Oscar surges to the all time high 5 victories. Lesline Connor takes back the female division.

EDITION: 11th Molokai Challenge
YEAR: 1986
- Oscar wins his 4th consecutive title. Julie Leach beats Conner for the female division.

EDITION: 10th Molokai Challenge
YEAR: 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.

EDITION: 8th and 9th Molokai Challenge
YEAR: 1983 – 1984
- Enter Oscar Chalupski from South Africa who wins them both back to back!

EDITION: 6th and 7th Molokai Challenge
YEAR: 1981 & 1982
- Grant Kenny wins again making a 4 year win streak

EDITION: 5th Molokai Challenge
YEAR: 1980
- Eve Anderson became the first female competitor and Chuck Bennett, a paraplegic, was the first physically challenged entrant. Grant Kenny repeats as winner


EDITION: 4th Molokai Challenge
YEAR: 1979
- 18 Entrants FinishedPaddlers made the crossing, including the first international competitor, Grant Kenny of Australia, who won the race in 5:37:05.

EDITION: 3rd Molokai Challenge
YEAR: 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.

EDITION: 2nd Molokai Challenge
YEAR: 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.

EDITION: 1st Molokai Challenge
YEAR: 1976
- Doc Adams paddled for 7 hours, 30 minutes in his first effort

kanakaikaika.com --> molokai challenge history

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