The Toronto Maple Leafs have played against 39 other NHL teams in their existence.
Rk  Franchise  GP  W  L  T  OL  PTS  PTS%  GF  GA  GF/G  GA/G 

1  Montreal Canadiens  740  297  341  88  14  696  .470  2051  2259  2.77  3.05

For simplicity sake, it’s a record of 297355. The 88 ties may as well have never happened for our purposes, because they’re currently not in the NHL, and they count as a stalemate anyway.
What’s the challenge?
The challenge: win 59 more games than the Canadiens do. In basic algebra terms, we can have x=the number of games the Canadiens win, and then subtract 59.
We’ll be making some assumptions here: the salary cap will continue to be in place and rise in a similar fashion that it does now, and both teams continue to play each other four times a year. The current overtime/shootout rules will be in effect still as well. Also, although it can’t quite be quantified, we’ll just assume that there’s no extra voodoo surrounding the games: just two teams playing against each other, where the better team usually wins.
Years 17
We’ll start by the first seven years, coincidentally the first seven years of John Tavares as a Maple Leaf. Barring something catastrophic, the Leafs appear to be in better shape than the Canadiens for pretty much the entirety of this contract, and at the very least the next 45. The Leafs swept the season series 40 last season, but we all know that’s not too easy.
The Leafs and Habs will face each other 28 times over the course of the Tavares deal, 14 each home and away. Assuming the Leafs win three of four per year, that’s of 21/28 wins… but only 14 more wins than the Canadiens.
The only issue? Actually winning 21 of 28 games is a pretty insane pace, even for what’s supposed to be one of the better teams in the NHL. For example, if you look at one of the league’s best teams since 200506 in Pittsburgh, and compare them to… their history against the Buffalo Sabres since then, Pittsburgh has dominated with a rate of 32 wins in their 46 matchups, but that’s still only a 69.5% win ratio. For no real good reason in this exercise, we’ll assume the Leafs are Pittsburgh and the Canadiens are Buffalo, for years 17.
The difference between 75% and 69.5% over seven years is only a win and a half (21 vs. 19.46), but since you can’t get half a win, let’s round it to two.
The Leafs go 199 against the Habs over seven years, and end up with an all time record of 31636488. By winning ten more games than the Habs, they now need 49 more wins than the Habs. Here’s one way that could break down.
Year  Wins  Losses  Win differential needed  Total wins in future 
2019  300  356  57  3 
2020  303  357  55  6 
2021  306  358  53  9 
2022  309  359  51  12 
2023  311  361  51  14 
2024  313  363  51  16 
2025  316  364  49  19 
The next x years
I’ve noticed a pattern. It’s kind of obvious, but because the teams play each other four times a year, the Leafs have to win 3 of 4 to make up any ground: otherwise they’re breaking even.
They could go on a streak and win 14 in a row like the Habs did for a while, but basic NHL probabilities tell us that’s pretty unlikely.
Let’s assume the Habs remain mostly incompetent, and the Leafs remain well run.
 One out of every ten years the Leafs win four in a row.
 Two out of every ten years the Habs win three of four.
 Three out of every ten years the Leafs and Habs spilt 22.
 The other four years, the Leafs win three of four.
For the first ten years, for simplicity’s sake, we’ll just have all those events happen in order.
Season  Wins  Losses  Win differential needed  Total wins in future 
2026  320  364  45  23 
2027  321  367  47  24 
2028  322  370  49  25 
2029  324  372  49  27 
2030  326  374  49  29 
2031  328  376  49  31 
2032  331  377  47  34 
2033  334  378  45  37 
2034  337  379  43  40 
2035  340  380  41  43 
In those ten years, the Leafs earned an average win differential of 0.8 per season, as they picked up a net gain of eight wins over that tenyear span.
If we continue rate of growth like this into the future, we’re still looking at the Leafs picking up less than one win differential on average per season, despite winning or tying the season series eight out of ten times.
If we divide the 41 wins needed left by 0.8, we get 51.25. Which mean it’d still be another 51 years after 2035 before the the Leafs even things up against the Habs, or 2086. And that’s still considering a pretty great domination.
My math is probably flawed somewhere along the way, but you probably get the point. While they may not have the better team on ice until 2086, one thing that Habs fans will probably be able to hold over their head is the alltime headtohead record against the Leafs.
The Leads beat the Hans every game for the next 7 years