Coming off their disappointing season the Maple Leafs once retooled by dipping into the free agent market. They added Pavel Kubina, Michael Peca, and Hal Gill to go along with new Goalie Andrew Raycroft. The trade has to be one of the worst in Maple Leaf history and put GM John Ferguson Jr. into a hole that he was never able to dig himself out of. Raycroft set a team record with 37 wins but had a mediocre 2.99 GAA and .894 SAV%.
For most of the first three months the Maple Leafs played mediocre hockey, as they headed into the New Year with a 17-17-6 record. In January the Leafs started playing better despite losing Peca for the season with a knee injury. The Leafs actually stayed in playoff contention until the very end of the season as they held destiny in their own hands in the final week playing the New York Islanders and Montreal Canadiens in the final two games. However, a 5-2 loss to the Islanders put the Leafs on the brink as they needed a win over the Habs and an Islanders loss to get in. Led by three assists from Mats Sundin the Leafs would do their part beating the Canadiens 6-5 to knock their long time rivals out of contention. However, the Islanders would win their final game of the season against the Devils. New Jersey who had started Martin Brodeur in 18 straight games sat him out in the final game of the season. The Islanders took the last playoff spot form the Leafs who finished 40-31-11 out of the playoffs by one point.
Ironically, as the Leafs stumbled from one goalie to another, the 2006-07 season saw they draft an unknown goalie from Manitoba in the 3rd round. He was James Reimer.