The winner of each series will meet in the second round.
Though this Jets franchise has never met the Oilers in the postseason, the two cities have quite the playoff history. The original Winnipeg Jets franchise took on the Oilers six times in the playoffs between 1983-1990, with Edmonton winning each time.
The Leafs - who've made the postseason in five straight seasons - will look to advance past the first round for the first time since 2004.
Toronto won the season series against Montreal 7-3, while Edmonton owned a 7-2 record against the Jets.
The playoffs begin Saturday for U.S. teams while the North Division games are expected to begin no earlier than next Wednesday.