The 93rd season for the Canadiens began with a shocking announcement that team captain Saku Koivu was suffering from intra-abdominal non-Hodgkins lymphoma, a form of cancer. This condition kept him out of all but three games in the regular season. On October 5, to respond to Koivu's absence, General Manager Andre Savard signed veteran forward Doug Gilmour to address the absence. The team began the season hovering around the .500 mark, but a five-game winning streak to end November, highlighted by spectacular performances by goaltender Jose Theodore, allowed the Canadiens to climb into the playoff mix. Around this time, Savard added offensive power to the team by acquiring Donald Audette and Shaun Van Allen from the Dallas Stars in exchange for Martin Rucinsky and Benoit Brunet. Head Coach Michel Therrien and the Canadiens had a rough December, posting a record of 4–8–2–1 while the newly acquired Audette had his forearm tendons sliced by the skate of New York Rangers forward Radek Dvorak. His season was jeopardized. Despite the inconsistency of the team, Theodore was spectacular in net. In January, the Canadiens played more .500 hockey, which prompted Savard to make a change. He traded forward Brian Savage to the Phoenix Coyotes in exchange for Sergei Berezin. The regular season went on hold for two weeks while the 2002 Winter Olympics were taking place. When play resumed, Jose Theodore took matters into his own hands and carried the Habs into the playoffs, finishing the regular season with a record of 30–24–10, seven shutouts and a goals against average of 2.11. In the 80th game of the regular season, captain Saku Koivu returned from treatment and played his first game of the season against the Ottawa Senators. He played for the team for the rest of the season. The Canadiens made the playoffs with a record of 36–31–12–3 behind the play of eventual Hart Memorial Trophy winner Jose Thoedore.
The Canadiens finished the regular season having allowed the fewest power play goals, with just 38.
In the first round of the playoffs, the Canadiens were matched against the Boston Bruins, who finished first overall in the Eastern Conference. Donald Audette lead the way with three goals and Saku Koivu had a goal and an assist to win game one 5–2 for Montreal. Game 2 would prove to be a back-and-forth affair, as both teams traded momentum. Boston won the game by a score of 6–4 despite a four-point performance from the Canadien Richard Zednik. The series shifted to Montreal, and the Canadiens won Game 3 5–3 through by a four-point performance by Koivu. This gave Montreal a 2–1 series lead. The Bruins responded in Game 4 as they won easily, 5–2. Theodore rose to the occasion in Game 5, stopping 43 of 44 shots for a 2–1 win to give the Canadiens a 3–2 series lead going back to the Molson Centre. Theodore was spectacular again in Game 6, and Yanic Perreault scored the game-winning goal to give the Canadiens a 2–1 victory. The Canadiens won the series in six games, upsetting the Conference's top seed.
The Canadiens faced the Carolina Hurricanes in the second round of the playoffs. The Hurricanes won Game 1 2–0 as Hurricanes goaltender Kevin Weekes was awarded the shutout. The Carolina Hurricanes dominated the Canadiens outshooting them 46 to 16, but Theodore only yielded one goal and Koivu had a goal and an assist and the Canadiens won Game 2 4–1 to tie the series. Game 3 went to overtime and due to the heroics of Theodore, he kept his team in the game. The Habs would win Game 3 just over two minutes into overtime on a goal by Donald Audette, giving the Canadiens the series lead. The Habs had momentum in Game 4, establishing a 3–0 lead early in the third period of Game 4. The Hurricanes, however, would score three-straight goals to send the game to overtime, where 'Canes defenceman Niclas Wallin ended the game in overtime to tie the series at 2–2. With newly gained series momemntum, the Hurricanes would win the next two games to win take the series at 4–2, outscoring Montreal 13–3 in the process.