2004 Round 1 and yes Round 2
Contrary to modern Leafs’ fan expectations, the Stanley Cup series actually has more than one round. Leafs beat Ottawa 4 games to 3 in Round 1, only to lose in Round 2 to Phillie 4-2. This, as unimaginable as this could be, was the last time Leafs won one, as in ONE, round of the playoffs.