Woolcock started cycling in 1997 as a 15-year-old and four years later he signed his first pro contract with Omega, an amateur road team at the time.
In the years that followed, he represented South Africa on more than 10 occasions, winning events such as the Tour of Egypt abroad and Jock Classic locally before moving off-road.
“My switch to the mountain bike happened more by chance,” admitted Woolcock.
He did his first race in 2010 in the colours of Medscheme and finished third, an achievement that planted a seed that would later blossom into a fully-fledged mountain biking career.
Riding for Bonitas the following year, his career spun in a new direction when he was offered the opportunity to join RE:CM’s new mountain bike team.
“Neil MacDonald and myself immediately put up our hands to join the team because we were the most avid mountain bikers in the group of roadies; and that’s where my mountain bike career started.”
Alongside the former South African national road racing captain, Woolcock became one of the country’s most dominant forces on the mountain bike.
“I think one of my highlights would have to be my first mountain bike stage race win with Neil at joBerg2C. It was our first stage race with the new team.
“That was a big highlight in my career, having come across from the road and all of a sudden winning what was then a special event.”
While his podiums at national events were another highlight, Woolcock said it was “unfortunate” he had never won a national title.
“That’s something I’ve been really close to a couple of times, but it’s eluded me my whole career. I’m still, to this day, a bit irritated about that, but that’s how it goes.”
With just one other regret – not converting to mountain biking earlier – the 35-year-old said, in hindsight, he was satisfied with his 20 years on the bike.
“It is a hard sport and there have been many times where I’ve questioned why I was doing it to myself, but, that being said, I don’t think I would’ve done anything differently.
“It’s opened so many doors for me throughout my life – job opportunities, people I’ve met and the places I’ve seen – so it’s definitely been a blessing and I’m happy I could do it.”
While he will bid farewell to professional racing, Woolcock said he was by no means done with the bike and, having joined the Specialized team in a sales position, would race as often as time would allow.
“I still could race at a high level for another two or three years, but the opportunities are a lot less than a couple of years ago. When the opportunity from Specialized fell in my lap it was a bit of a no-brainer to take it.”
This season, Woolcock proved that he is by no means a spent force after winning the Winelands Encounter in April, the Great Zuurberg Trek in May, his second TrailSeeker Series title at the end of September and most recently the Tour de Plett.
He will line up alongside BCX teammate HB Kruger for one last time when the three-day Wines2Whales gets underway from Lourensford in Somerset West tomorrow.
With Cape Pioneer Trek winners Alan Hatherly and Matt Beers and joBerg2C, sani2C and Berg and Bush champions Philip Buys and Matthys Beukes on the start line, Woolcock will undoubtedly be in for one more tough battle in his distinguished career.