[4] During his junior college years, Tan started Laser Sailing and participated in the Inter School Championship and various races in Singapore.
[4] Tan sailed for Singapore in the OK class at the 1995 Southeast Asian Games and won the silver medal.
[1] Tan made his official debut at the 2000 Summer Olympics in Sydney, where he placed close to last (thirty-eighth) in the Laser class with a net grade of 275, finishing closer behind Malta's Mario Aquilina by a three-point deficit.
[4][5] At the 2004 Summer Olympics in Athens, Tan qualified in the Laser class by placing again, close to last, at seventy-seventh and obtaining a berth from the World Championships in Bodrum, Turkey.
Tan posted a net grade of 322 points and improved his position to thirty-seventh in a fleet of forty-two sailors.