The Toronto Maple Leafs have played against 39 other NHL teams in their existence.

For simplicity sake, it’s a record of 297-355. 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.

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.

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 4-5. The Leafs swept the season series 4-0 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 2005-06 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 1-7.

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 19-9 against the Habs over seven years, and end up with an all time record of 316-364-88. 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.

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.

For the first ten years, for simplicity’s sake, we’ll just have all those events happen in order.

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 ten-year 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 all-time head-to-head record against the Leafs.