There is a high possibility that the Oilers go farther than the Leafs.
Let's be real, if the Leafs make it to the SCF it would be one of the toughest roads to the SCF in a long, long time. They have recent 2x champs, Boston who is having a historic season and then probably Carolina (I don't think Svechnikov injury changes the fact that they're just a better team than NJ and NY).
Oilers road consists of teams that are all below the Leafs in the standings. Their hardest opponent is probably Dallas or Colorado if they meet them.
No one in their own division is stopping them.
In contrast, Colorado faced 3 absolutely garbage goalies in the Western Conference before beating a Tampa team without Brayden Point.
The Leafs have had plenty of easy roads (the year Columbus beat them, the year the Habs beat them etc) and they failed to take advantage so this is all on them. Have to beat the best to be the best (at least for the Leafs this season).