Picking the Toronto Maple Leafs to win the Stanley Cup is a bet that, in every capacity, nobody in the world has won for over five decades now.

But if the Leafs are ever going to break the Stanley Cup curse, well, they have to start somewhere.

The Stanley Cup is often called the toughest trophy in sports to win, and with good reason: it’s a grueling grind of anywhere from between 16 to 28 extra games at the end of the season to be named the NHL’s champion for any given year.

Toronto’s aiming to win their first title since they pulled it off in 1967, and is still searching for their first playoff series win since 2004.

A first-round matchup against the Tampa Bay Lightning appears to be all but set in stone, giving the Leafs a second chance at their Atlantic Division foes who knocked them out of last year’s playoffs.

But should they get out of that elusive first round, there’s three other series that Toronto would have to get through to be named the NHL’s champion for the 2022-23 season.

As of today, here’s what the most likely matchup is for the Leafs’ Stanley Cup route, via Sports Interaction’s Stanley Cup odds:

Round 1: Tampa Bay Lightning

As mentioned, Toronto and Tampa went the full length of a seven-game series last year, before the Lightning topped Toronto 2-1 on home ice.

Based on the current standings, Toronto would have home ice advantage, as they currently sit four games up on the Lightning with a game in hand.

Tampa has the sixth-best best odds advancing out of the Eastern Conference (10.35), while Toronto sits third (6.42).

Round 2: Boston Bruins

If Toronto wants to fully exorcise their playoff demons, there’s a better chance than not that they’d be up against a familiar foe in the Boston Bruins, who have the best odds to both advance out of the Eastern Conference (3.13), as well as the best Stanley Cup odds league-wide (4.47).

Boston is currently slated to face the New York Islanders in the opening round of the playoffs, though there’s quite the battle developing in the bottom half of the Eastern Conference for the final wildcard playoff spot.

Eastern Conference Final: Carolina Hurricanes

Can we call it a “rematch” if the last time these two met in the Eastern Conference Final was way back in 2002? While Carolina’s Andrei Svechnikov is in line for a season-ending knee surgery, the Hurricanes are still a roster loaded with plenty of talent throughout their lineup even without one of their top dogs.

Carolina has the second-best odds to win the East (5.59), trailing only Boston, while they’re also ahead of the New Jersey Devils (6.96), NY Rangers (8.88), Pittsburgh Penguins (19.96), and NY Islanders (31.09) amongst divisional foes, while they also top the Florida Panthers (31.75) who could cross over from the Atlantic Division.

If nothing else, this hypothetical series would be a fun one for fans who recall the duels between Mats Sundin and current Canes coach Rod Brind’Amour some 21 years back.

Stanley Cup Final: Colorado Avalanche

Who else but Colorado in the West?

Assuming Toronto has the juice to win 12 playoff games in the Eastern Conference, oddsmakers are backing the Colorado Avalanche to return to the Stanley Cup Final after winning it all last year.

Colorado (3.79) is the odds-on favourite to come out of the Western Conference this year, ahead of Vegas Golden Knights (6.17), Dallas Stars (6.71), Edmonton Oilers (7.18), Los Angeles Kings (9.39), Minnesota Wild (9.40), Seattle Kraken (11.99), Winnipeg Jets (13.07), and Calgary Flames (21.60).

The Avs are looking to be the first repeat winners since, well, the Tampa Bay Lightning pulled off the feat in 2020 and 2021.