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The 2023 NHL playoffs begin in one week, and two of the game's biggest stars will be looking to win their first Stanley Cup. Connor McDavid and Auston Matthews are already starting to run out of room in their trophy cases, but to this point, the Stanley Cup has eluded both players.

The Edmonton Oilers selected Connor McDavid with the No. 1 overall pick in the 2015 NHL Draft. One year later, Matthews went to the Toronto Maple Leafs with the top pick.

Now, McDavid and Matthews are arguably the top two players in the league. They have combined to win the Hart Trophy three times, the Art Ross Trophy four times and the Rocket Richard Trophy twice. Those totals will only keep climbing over the next decade.

Connor McDavid

Auston Matthews













Playoff Games



Playoff Points



The only hurdle remaining for each player is hoisting 35 pounds of silver and nickel alloy. Getting to that moment is perhaps the biggest challenge in all of sports, which is something that McDavid and Matthews are well aware of by now.

Matthews hasn't even seen the second round of the playoffs yet. He's been to the playoffs six times, and Toronto has lost in Game 7 four times. Those early exits haven't fallen on the shoulders of Matthews, but the Leafs must find a way to capitalize on their championship window.

McDavid and the Oilers have been a little more successful in the postseason, but they still haven't gotten any closer than eight wins away from a Stanley Cup. Edmonton reached the Western Conference Finals in 2022, where they were swept by the Colorado Avalanche. Despite falling short, McDavid was the best player in the postseason. He tallied 33 points, which led the league and equaled Matthews' career postseason point total.

This season, McDavid and Matthews can leave past playoff woes in the dust. They are both playing at an elite level, and they have teams that are fully capable of going all the way.

Matthews' Maple Leafs have a tougher path

The Maple Leafs are locked into second place in the Atlantic Division, and they will get a first-round matchup against the Tampa Bay Lightning for the second consecutive season. For the first time in years, the Lightning actually look somewhat vulnerable heading into the postseason.

  • Since the trade deadline, the Maple Leafs are just 9-5-3, but they have battled injuries and still produced some decent underlying numbers.
  • Toronto has controlled 52.66% of the expected goals at five-on-five, per Natural Stat Trick.
  • Matthews himself has hit his stride. In his last 19 games, he has led the Leafs with 11 goals, 14 assists, and 25 points. Matthews has to be at his best for Toronto to win its first Stanley Cup in 1967.
  • Matthews' strong supporting cast includes Mitchell Marner, William Nylander, John Tavares, Ryan O'Reilly and Morgan Rielly.

Toronto can match up with every team in the postseason, but the other two teams at the top of the Atlantic Division are just as strong as them. Their road to the Stanley Cup Final will be a brutal one. If Toronto can get the first-round monkey off its back against a team that has won the Eastern Conference in three straight seasons, it will likely have to face the Boston Bruins, perhaps the greatest regular-season team in NHL history.

Add in the conference finals, and the Leafs will probably have to face three very real Stanley Cup contenders before even reaching the final. Before they can worry about that, Matthews has to help lead the team to its first postseason series win since 2004.

McDavid's Oilers will need to knock off defending champs

On the other side of the bracket, the Oilers have a slightly more manageable path, and they seem to be peaking at the right time. 

  • Edmonton is 15-2-1 since the trade deadline, the NHL's best record in that span..
  • The red-hot Oilers have been led by McDavid, who is having the best season the NHL has seen since Mario Lemieux was torching the rest of the league in 1995-96. McDavid has surpassed 150 points on the season, and he can go ahead and clear some space on his shelves for another Hart Trophy.
  • We know McDavid is capable of carrying a flawed team for at least a couple of rounds in the playoffs. This year's team doesn't have as many cracks as last year's, and that makes the Oilers a favorite to win the Western Conference.

Leon Draisaitl, Zach Hyman, and Ryan Nugent-Hopkins give McDavid plenty of help up front, but the defense and goaltending have improved the most. The acquisition of first-pairing defender Mattias Ekholm has rounded out Edmonton's blue line, and Stuart Skinner has given the Oilers reliable goaltending all season. If he can keep that up in the playoffs, few teams will be able to stack up with Edmonton from the crease to the top line.

Getting through the Pacific Division, which also contains the Vegas Golden Knights and Los Angeles Kings won't be easy, though. Those teams are capable of emerging as the Western Conference champs, but neither of them have anyone who can keep up with McDavid when he is at his best.

The toughest potential series for the Oilers would be a Western Conference Finals rematch with the Avalanche. Despite some changes from last year's team, the Avs still boast a loaded roster and will be on a mission to win the Cup in back-to-back seasons. On top of that, Nathan MacKinnon is on the short list of players who actually can go toe-to-toe with McDavid. That would be a fun battle to watch, especially now that the Oilers have comparable firepower elsewhere.

McDavid and Matthews have rightfully earned top billing as the NHL's two biggest stars, and now it's time for them to etch their names on the Stanley Cup. Based solely on the gauntlet that Toronto must navigate, it seems like McDavid has the better chance to break through first in 2023, but Matthews and the Maple Leafs have all the parts you look for in a championship-caliber team.

If NHL fans are lucky, McDavid and Matthews even meet one another in the Stanley Cup Final.