Simon Christopher Lessing, MBE, (born 12 February 1971) is a British triathlete who won five International Triathlon Union (ITU) world titles (1992, 1995(2), 1996 and 1998).

Growing up, surfing and rugby were two of the major sports in Durban, but Lessing resisted the pressure to make the change to these activities.

He trained an average of 3 hours a day in his areas of interest: sailing, swimming, track, cross-country and duathlon.

His swim coach, David McCarney, encouraged Lessing to try a family oriented race he organised at Kloof High School.

[2] He was selected to represent South Africa in a biathlon but suffered a broken leg in an accident during a local triathlon.

[citation needed] Lessing moved to Britain at age 18 and continued his international sporting career in Europe.

In his first appearance at the Ironman World Championships (2004) he dropped out halfway into the bike leg, due to the high winds and problems with his back.