The race started in 1980, and initially it alternated years with the famous PE to East London race.

2014 Saw Hank McGregor shave just over half a minute off of  Sean Rice’s record  of 3hr 40 mins (2010). The Current full course race record is 3:39:50 held by Hank McGregor.

Men who have won the race twice include: Herman Chalupsky; Oscar Chalupsky; Paul Marais, Dawid Mocke, Peter Creese and Hank McGregor.

Women who have won the race twice include: Jean Wilson, Nikki Mocke, Michele Eray, Bianca Beavitt and Hayley Nixon

Hank McGregor has won the race a staggering 8 times with  Michelle Eray having  won the ladies race four times.

Out of the 26  races held so far, 4 have had strong north-westerly winds; 13 have had strong south-easterly winds; and 6 had ‘calm’ conditions and 2 had massive swell with little wind.

1980 Was the first ever Cape Point Challenge with Peter Creese winning in a lifesaving style ski in a time of 5:39:15.

1982 Tony Scott was the man of the moment winning in a time of 4:40:31

1984 there were 31 entries. The wind at Soetwater was blowing 28kts, 6 competitors withdrew before the start. 15 more retired before Tommy Tucker. The wind was measured at 47kts at Cape Point, making this the year the Cape Point Challenge legend was born. The winner, Oscar Chalupsky took 6:28:10  to complete the course.

1986 to 1993 Had a variety of legendary winners in the mix, Oscar Chalupsky, Peter Creese, Ian Boyd, Lee Mc Gregor and Paul Marais were winners of the Mens race.

1995 the organisers changed the course, which ran from Buffels to Cape Point and back to Fish Hoek due to very strong SE winds. Paul Marais won again.

1997 History was made and 2 ladies entered the race. Jean Wilson won  in a time of 5:43:13 and Junior Nikki (Lihou) Mocke taking 6:15:18 to complete the course. Peter Cole won in strong North Westerly conditions in a time of 4:39:25.

1999 to 2003 was dominated by the Chalupsky family with Oscar winning in 1999 and Herman winning 2 consecutive races in 2001 and 2003.

2005 organisers were forced to run the course from Fish Hoek to Cape Point and back (56km) due to high winds and excessive swell. There were 250 entrants this year. Dawid Mocke won his first CPC (4:16:50) and Nikki Mocke, her second in a time of 4:51:20).

2006 The decision was taken to stage the event annually starting in 2007

2007 Peter Cole lead for most of the race but was overtaken by Durban’s Daryl Bartho just 5km from the finish (in a time of 4:28:37), Bianca Beavitt won the ladies in a time of 5:47:26.

2008 The course was again changed to its current format to start in Scarborough. The compulsory 10 minute stop at Buffels Bay was taken out and paddlers rounded Cape Point and headed straight downwind with the southeaster to Fish Hoek – a distance of 50 km. Hank McGregor won his first singles title (3:54:55), while Michelle Eray won her first title (4:26:58).

2009 Due to a howling 30kt southeaster blowing at Cape Point, the course started in Simons Town. Paddlers paddled to Buffels Bay and then out to Cape Point, where they rounded a buoy and back to Fish Hoek. Dawid Mocke triumphed for a second time (3:44:39) with Michelle Eray also picking up her second title (4:26:58).

2010 Flat glassy conditions greeted the paddlers with Sean Rice taking control of star studded field as he rounded Cape Point to set a new record of 3hr 40mins and 43 seconds (The Current race record). Michele Eray won the race for the 3rd time (4:09:29).

2011 Again, the conditions were picture perfect with Hank McGregor taking control once rounding Cape Point, to take his second title (3:47:46). Alexa Cole won the ladies (4:35:36).

2012  The race started flat as a pancake, but the NW wind picked up steadily throughout the morning. This year saw the closest finish ever with 7 guys sprinting for the line honours… Hank Mc Gregor, Sean Rice, Grant V D Walt, Simon Van Gysen, Jasper Mocke, Richard von Wildermann & Dawid Mocke. The difference Hank in first place and Dawid in 7th place was a slender 20 seconds. Michele Eray won her 4th Cape Point Challenge title. (4:32:43)

2013 Due to a very strong southeaster and a huge swell on the Altantic side, the course started in Simons Town again. Paddlers paddled to Cape Point, where they rounded a buoy and back to Fish Hoek. Hank McGregor scooped his 4th win (3:41:20) with Nikki Mocke taking the ladies title (4:24:43). At prizegiving, Hank commented on the size of the surf and credited the organisers with a good decision in not going around the point!

2014  Saw massive swell along the coast to Cape Point.  The majority of the field took a wide line on the Atlantic side with a relatively flat paddle home.  There was a big bunch of paddlers at Cape Point pushing the pace, but Hank Mc Gregor managed to push harder on the home straight to win the men’s in a new course record just under 4 hours. (3:39:50 *NEW COURSE RECORD*) with Chloe Bunnet taking the ladies race (4:49:45).

2015 The dreaded North Wester arrived. A few small runs to the point and then a long hard slog to the beach.  Not the strongest North Wester we’ve seen in the race, but a tough one none the less. Bianca Beavitt enjoyed the head wind and won the ladies with Hank breaking away early in the race to win the Mens title once again.

2016 “Silky and flat” was how first time ladies winner Hayley Nixon described the race winning in a time of 4:39:35. There was a light South Easter which provided some assistance to the paddler coming home. Hank won his 6th consecutive title (3:57:50) (7th title overall)

2017 Was the 25th Cape Point Challenge and we celebrated “perfect” conditions. With a light South Easter building throughout the day giving paddlers a classic “millers run” on the last stretch of their journey. Hayley Nixon won the ladies (4:43:52) with local Fish Hoek club member Kenny Rice taking his first win in the men’s race (4:00:52).

2018 Will never be forgotten. With winds in excess of 30 knots the course started at Simons Town Long Beach and planned to head along the coast around a buoy at Buffels Bay and out to Cape Point.  With such extreme conditions paddlers were forced to turn at the NSRI boat in Buffels bay and head for Fish Hoek beach.  Anyone to complete this one can wear the T-shirt with pride.  Bianca Beavitt won her 3rd title in the event spread over 10 years with Hank winning his 8th title.

2019 For the 2nd year in a row, the race did not go around Cape Point, A huge SW swell 5m plus and SW winds made for a really tough outing. Paddlers started at Fish Hoek beach and paddled via Glencairn to a turn buoy outside of Cape Point, making it a proper 54km outing, Here paddlers got a true reflection of the size of the swell hitting the SW tip of Africa, Both Kenny Rice and Chloe Bunnet won their 2nd titles.

2020 Again saw the paddlers not rounding Cape Point. With 30 knot plus SE winds, the race became a 3 lap course starting in Simons Town, with a turn buoy at Millers and back to a Simons Town turn buoy. On the final Millers turn it was full steam ahead on the Iconic Millers Run and back to Fish Hoek. Kenny Rice won his 3rd title in 4 years and Melanie van Niekerk won the ladies race for the first time.