The first stage of the three-day mountain-bike race saw competitors cover 48km from the Boschendal Wine Estate to Le Franschhoek Hotel.
Woolcock and Roux were first home in 1:54:22, ahead of Cobus Swanepoel and Neville Cragg (1:57:19). Dawid de Bruin and Michael Dundulakis filled the third podium spot.
The 2017 champion, when he partnered HB Kruger to the title, Woolcock is using this opportunity to help to develop his team-mate’s career.
He has been coaching Roux, who turns 20 tomorrow, for the past two years and said they felt good going into the race.
“We managed to ride away on the first climb and from there it was just a matter of controlling things,” he said.
“I was able to use my experience to pass on some advice to him about where to ride hard and where to be a little bit more cautious, so it was a good day for both of us.”
Woolcock added that, as usual, the trails set up for the race had provided a clear indication of what the Cape Winelands had to offer avid mountain-bikers.
“Starting from Boschendal there were some pretty decent, steep climbs and nice single-track.
“From there we headed over to Franschhoek, which is a bit more open with gravel roads and jeep tracks.
“But it is still fairly rough and offers typical mountain-bike terrain, so that was really cool.”
In the women’s race, Alta Kriegler and Sunette Beyers were first across the line, while Andrew Marsh and Anneke Viljoen lead the mixed category.
Cobus Barnard has a two-minute advantage over Simon Bothner in the men’s solo section and Amy McDougall is a clear leader in the women’s category.
Tomorrow’s stage will start and finish at Le Franschhoek Hotel, covering 48km with a total elevation of 1 144 metres.