Wooldridge won gold in the 4000m team pursuit at the Athens Olympics in 2004, also claiming four world titles in the same discipline.
Wooldridge is being remembered for his efforts in supporting young cyclists.
Cycling NSW confirmed the cyclist's death in a statement.
Stephen was an inspirational figure in track cycling, particularly in his home state of NSW," the governing body said.
"Cycling NSW's thoughts are with Stephen's family and his friends during this difficult time."
Cycling promoter Phill Bates wrote in Ride Media: "In our sport of cycling, you see some conquer with lesser effort than others. Then you witness those that continue to work harder and reach even greater heights.
"Tragically today he gave his life away leaving behind a son and daughter, family and friends just short of his 40th birthday.
"Steve achieved many cycling accolades, NSW Hall of fame but also a degree in engineering and was playing a pivotal role at UNSW. His infectious smile, gentleman attitude on and off the bike made him a very special person.
"We are better for knowing him and worse off for losing him."
Wooldridge found passion in competitive cycling as a child, but wasn't able to break through to the pinnacle at a young age.
After missing out on the World Junior Championships, Wooldridge concentrated on university studies - completing a Bachelor of Technology Management in Manufacturing.
Elite cycling was never far off his radar however, deciding to make a play at national selection ahead of the Sydney Olympic Games.
Focusing back on the sport initially paid off, earning a place on the nine-man squad for the Games, before a decision was made to go to a seven-man squad - Wooldridge one of the unlucky two to miss out.
Not the first time the Order of Australia medallist missed out, the snub spurred Wooldridge on and four years later, he was Olympic champion in Athens.