Will Oilers’ Connor McDavid, Maple Leafs’ Auston Matthews finally win first Stanley Cup in 2023-24?

Drafted No. 1 overall almost exactly one year apart, Connor McDavid and Auston Matthews are arguably the top two players in the NHL at this point. They have racked up hardware throughout their 15 combined seasons, but neither player has lifted the Stanley Cup. Can one of them change that in the 2023-24 season?

McDavid and Matthews have already asserted their dominance over the rest of the NHL, especially in the regular season. Since the 2016-17 season, the first with both players in the league, McDavid and Matthews have put up some gaudy numbers.

Between them, McDavid and Matthews have combined for a Calder Trophy, three Maurice Richard trophies, five Art Ross trophies and four Hart trophies. They have garnered a slew of accolades, but neither has been able to capture the 35 pounds of nickel and silver every player covets.

As much success as McDavid and Matthews have had in the regular season, that has not translated to the playoffs. Matthews and the Toronto Maple Leafs have advanced beyond the second round once since he’s been there, while the closest McDavid and the Edmonton Oilers have gotten is eight wins away from a Stanley Cup.

In the 2023 Stanley Cup Playoffs, Matthews helped the Maple Leafs get the monkey off their back by reaching the second round for the first time since 2004. Unfortunately for Matthews and the entire city of Toronto, the team won just one more game after that, as the Florida Panthers defeated them in five games in the Eastern Conference semifinals.

Matthews was excellent in the Maple Leafs’ first-round victory over the Tampa Bay Lightning, tallying five goals and four assists in 10 games. Then Matthews struggled to produce against the Panthers. He notched just two assists in five games, leaving something to be desired on the NHL’s biggest stage.

The lack of consistency has been an issue for Matthews, and his Toronto teammates, in recent postseason history. Don’t get me wrong: Matthews has 22 goals and 22 assists in 50 career playoff games, which 99% of players would take without thinking twice. It just seems like we have yet to see Matthews really play at his peak in the playoffs so far.

That hasn’t necessarily been an issue for McDavid, who has powered the Oilers to three playoff series wins in the last two years. In 2022, McDavid looked downright unstoppable as he piled up 10 goals and 23 assists in 16 games. His 33 points led all playoff scorers despite the fact that the Colorado Avalanche swept the Oilers in the Western Conference Final.

Last season, McDavid once again dominated with eight goals and 12 assists in 12 games. Once again, it wasn’t enough to get his team within reach of the Cup. The eventual champion Vegas Golden Knights took down the Oilers, 4-2, in the second round.

Coming into the 2023-24 season, Caesars Sportsbook currently has the Oilers and Maple Leafs as two of the biggest favorites to win the Cup with +900 odds. What will it take for McDavid and Matthews to deliver on that buzz and get over the hump?

For McDavid and the Oilers, the answer is relatively simple: Edmonton needs to do a better job of keeping the puck out of its own net. Over the last two postseasons, the Oilers’ goaltenders have combined to allow 5.05 goals saved above average, per Natural Stat Trick. That won’t win the Stanley Cup — unless you’re the 2022 Avalanche, a very unique juggernaut.

The good news for the Oilers is that McDavid should get more help from the blue line, with Mattias Ekholm entering his first full year with the team. After acquiring Ekholm from the Nashville Predators ahead of the trade deadline, Edmonton’s defensive numbers improved quite a bit, and that will only continue in 2023-24.

The bad news for the Oilers is that they are running it back with the goaltending tandem of Stuart Skinner and Jack Campbell. Skinner finished second in Calder Trophy voting after an exceptional regular season, but he struggled in the playoffs. Conversely, Campbell had a disastrous regular season, but by the time he recovered in the postseason, it was too late.

One of those two will have to put it all together for the Oilers to win the Cup in 2024. If Campbell or Skinner can provide even slightly above average goaltending in the playoffs, that will be enough for McDavid and the Oilers’ offense to get the job done.

The solution for Matthews and the Maple Leafs is a little less straightforward. It seems like a variety of issues have led to playoff disappointments of late. In 2023, it was the fact that the Toronto offense went quiet as Panthers netminder Sergei Bobrovsky stonewalled the Leafs for five games.

The answer might be as simple as everything finally clicking at the right time. Last season, Jack Eichel, Mark Stone and Shea Theodore played some of the best hockey of their careers while leading the Golden Knights to a Stanley Cup. In 2022, the same thing happened with players like Nathan MacKinnon and Cale Makar for the Avalanche.

It’s hard to deny that the Maple Leafs have the pieces of a Cup contender. Matthews has plenty of support around him, with Mitch Marner and William Nylander cracking our ranking of the top 10 centers. Morgan Rielly and T.J. Brodie lead a more-than-capable stable of defensemen. Toronto has its own goaltending questions, but Ilya Samsonov is a serviceable option between the pipes.

At this point, it’s about Toronto figuring out a way to make the whole greater than the sum of its parts. That might have to start with an otherworldly playoff performance from Matthews, who certainly has the skill and will to put the team on his shoulders.

When it comes to superstar-caliber players like McDavid and Matthews, playoff breakthroughs seem more like a matter of “if,” not “when.” Heading into the 2023-24 season, “when” looks a lot like “now.”