On this date in 1999, the Flyers lost to the Maple Leafs in the Air Canada Centre, 2-1 in overtime, in Game Five of their Eastern Conference Quarterfinal series.
The Flyers Keith Jones opened the scoring in the game with a goal at 1:52 of the first period.
Toronto defenseman Dimitri Yushkevich scored a power play goal at 9:16 of the first period to tie the score at 1-1.
After a scoreless second and third period, Toronto's Yanic Perreault would score a goal at 11:51 of the first overtime period to give the Maple Leafs the win.
Maple Leafs goaltender Curtis Joseph stopped 33 of 34 Flyers shots to record the win, while Flyers goaltender John Vanbiesbrouck allowed two goals on 34 shots faced to post the loss.
The Flyers would lose to Toronto in Philadelphia, 1-0, in Game Six on May 2. The Flyers would be shutout the final 129:59 minutes of play in the series and lose the series, four games to two.