- The event was conceptualized by the Oakley Sports Marketing Manager Seth Hulley. A former professional surfer, Seth dreamed up the Oakley X-Over Challenge as a way to have something different to the standard style of events that take place in the country.
- Gareth ‘Soldierboy’ McLellan was the EFC Africa Mixed Martial Arts EFC Middleweight Champ 2014, but placed 12th, in the inaugural Oakley X-Over Challenge which had 12 competitors.
- In the surfing event 2014 World Surf League Championship Tour surfer Jordy Smith scored a perfect 10-point ride for both of his scoring waves. Greg Minnaar and Bob Skinstad came in second and third in the surf event.
- During the Golf event at The Links golf course in St Francis Bay, 11-times world champion Kelly Slater popped in to say hello. John Smit was proud to meet Kelly, but Kelly was just as proud to meet John.
- Ultra trail running phenomenon Ryan Sandes was the surprise in the Mountain Bike division of the Oakley X Over. There were no surprises with three-time world champion Greg Minnaar coming in first, with Kevin Evans in second. Triathlete Raynard Tissink was in third with Sandes the surprise in fourth.
- New faces for the 2015 event so far are Dale Steyn, and Superbike Rider Lance Isaacs.
- Former Springbok Captain and current Sharks CEO John Smit surprised everyone by his skills in the water during the surf event. Having not surfed too much in the past, John paddled out and picked up two decent waves of the bat, riding them all the way through to the inside in front of the cheering crowd.
- Prior to the 2014 event Ryan Sandes went for a professional golfing lesson at the SA Golf Institute at Westlake. Ryan reckoned that he was stiffer the next day than after a 100-mile trail race.
Highlights of the 2014 event can be viewed here https://www.youtube.com/watch?v=0Ui2s5H9wbI