Michalchuk first entered the world professional snowboarding circuit in 1998 at the age of twenty-one after he gained qualification for the 1998 Winter Olympics as a member of the Canadian team. During the games he would go on to qualify for the finals with an equal best score but his performance would drop and he would eventually finish in 8th position. During the 1998 season he would achieve his highest honor during that year's world cup in the United States finishing third in the half-pipe event.

The following seasons became mostly disappointing ones for Michalchuk after he was plagued by several injuries including blowing out his right knee and a recurring achilles tendon injury and it would not be until 2001 when he would again compete on a regular basis. His only glory during this time came at the end of 2000 when competing in the Nike All Conditions Gear Indoor competition he would take out first place after landing a "near flawless" double back flip during the quarter-pipe competition and taking home a car and $32,000 dollars in prize money.

2001 saw Michalchuk injury free and compete in nearly a full half-pipe world cup circuit where he would achieve several top ten positions including taking a third placing during the event in Whistler.

Michalchuk gained 2002 Winter Olympic qualification after a strong performance in Alpe d'Huez, France in early 2002 but after making his second Olympics he performed poorly failing to qualify for the finals in the half-pipe event and eventually finished a disappointing twenty-seventh.

Since the 2002 Olympics Michalchuk has been further hampered by injury and his performances have suffered, between 2002 and 2005 he only achieved a sole top ten placing on the world cup circuit and then took the entire 2006 season off from professional touring.

Michalchuk became the first snowboarder to perform a double back flip in halfpipe competition during 1997 around the time when he first turned professional. After performing the move he gained much media attention and would then often use the move in many professional competitions.

The Michalchuk was a trick invented by Michael Michalchuk and has since become his signature move. It involves a back flip while doing a 540 and at the same time chanting Michalchuk three times.