Fleury compiled a 35–18–7 record in 2008–09 to help the Penguins to a fourth-place finish in the Eastern Conference, entering the 2009 playoffs as the defending Prince of Wales champions. Fleury was a major factor in the first round against the Penguins' intrastate rivals the Philadelphia Flyers. In Game 2 at home, with a 2–1 deficit late in the third, Fleury made a key toe save against Flyers top goal scorer Jeff Carter which was eventually pivotal as the Penguins tied the game late in the 3rd and won late in overtime. After the Flyers won Game 3 comfortably, Fleury once again stole a game for the Penguins in Game 4, stopping 43 shots to keep a surging Flyers line-up at bay and ensure a 3–1 lead. The Flyers won in Pittsburgh in Game 5, but Fleury saved another performance for the final period of Game 6. After initially letting in 3 goals, Fleury did not allow another as the Penguins rallied from a 3–0 deficit to win 5–3. The Penguins went the full distance in the second round against the Washington Capitals. In the deciding game seven, Fleury made a key breakaway glove save early in the contest against Capitals superstar Alexander Ovechkin, helping the Penguins eliminate Washington by a 6–2 score.