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Philadelphia Flyers right wing Matvei Michkov plays the puck against New Jersey Devils defenseman Simon Nemec and goaltender Jacob Markstrom (John Jones-Imagn Images)

When Will the Flyers’ Cup Window Begin and End?

Originally posted on The Hockey Writers
By Justin Giampietro | Last updated Dec 31, 2025 10:05 AM ET

The Philadelphia Flyers are in the midst of a surprise hunt for a playoff spot. With a 20–11–7 record, heading to the postseason for the first time since the COVID-19 pandemic feels like a real possibility. But even they know that doesn’t mean their Stanley Cup window has opened yet.

After all, the Orange and Black have spent the past few years building up the prospect pool, and a lot of those players are still developing. In this piece, we’ll pinpoint when the Flyers can realistically compete for Lord Stanley.

When Is a Player’s Prime?

To find the Flyers’ window, we first have to define when a player’s prime is. Old enough to be past the development stage, but young enough to disregard Father Time.

Fortunately, Dom Luszczyszyn of The Athletic crunched the numbers for an article a few months ago (from ‘As NHL free agency nears, how will players age on their new contracts?,’ The Athletic – June 5, 2025). Looking at that data, both forwards and defensemen are in their prime from ages 23 to 29, give or take.

Goalies are a bit trickier, but they appear to be about the same. A Hockey-Graphs piece, albeit on the older side—posted March 2014—outlines the data well.

These age ranges are admittedly not absolute, but rather an approximation of when a player should be at his best. That said, it can help us pinpoint the seasons when the Flyers should be at their peak, due to their top prospects entering their “prime.”

Identifying the Flyers’ Cup Window

I looked at the Flyers’ top prospects and roster players, and identified a mini window: 2029–30 to 2031–32. Let’s break it down.

I’ll preface by saying everything is secondary to Porter Martone and Matvei Michkov. Both of them have superstar upside—if and when they reach that level, the Cup window opens. In 2029–30, they will be 23 and 25, respectively. That may sound young, but it’s around that age where we should see them take the reins.

What makes 2029–30 such an important season is that not only will the prospects start to be impactful in the NHL, but some players on the team today should be at their peak (mid-to-late 20s, generally).

Jamie Drysdale, Tyson Foerster, Cam York, and Trevor Zegras will be between the ages of 27 and 29. Meanwhile, prospects like Denver Barkey, Oliver Bonk, Alex Bump, Spencer Gill, Jett Luchanko, Jack Nesbitt, and Egor Zavragin will all be 23 or above, old enough to be notable contributors on the team.

Don’t forget about Travis Konecny, Travis Sanheim, or Owen Tippett, either. They’ll be between the ages of 30 and 33—likely past their prime, but still helping the Orange and Black win games.

By 2029–30, the Flyers will have probably added win-now talent to the roster. If that’s the case, and Martone and Michkov are high-end producers (which seems likely enough), this should be a contender. There’d be superstars, stars, and depth throughout the lineup.

The next two seasons would presumably see some members of the 27–29-year-old group start to regress, and players like Konecny, Sanheim, and Tippett decline a bit more heavily. At the same time, however, players drafted between 2023 and 2025 would hit their peaks.

As I stated before, this whole thing runs through Martone and Michkov. So, as long as they’re playing like superstars, and the team around them hasn’t totally deteriorated, the Flyers’ window should be wide open. Neither of them will be 30 years old until 2034–35, mind you, and elite players typically fade a lot more gradually than standard ones.

What Does This Mean for the Flyers’ Future?

So, what does this all mean? Does nothing matter until another four years from now?

Well, that depends on how the Flyers want to attack this. If Martone and Michkov are the core, you can’t expect them to be the backbone of a championship team right now.

To elaborate, while Patrick Kane and Jonathan Toews won Cups early in their careers (which we all remember well…), they had Marián Hossa, Duncan Keith, Brent Seabrook, Patrick Sharp, and other in-their-prime stars to help out. The Flyers would need that kind of veteran talent, too.

Instead, the Dallas Stars might be a good model to follow. In 2022–23, they were led to the Western Conference Final by two 23-year-olds: Miro Heiskanen, who finished seventh in Norris Trophy voting, and Jason Robertson, who finished fourth in Hart Trophy voting. Of course, they weren’t the only good players on that roster, but those were the Goliaths.

Ultimately, I think the Flyers will be more like the Stars than those 2010s Blackhawks. Martone and Michkov won’t have a total juggernaut around them—they’ll lead the juggernaut.

In the meantime, being competitive is far from a doomsday scenario. Yes, getting another top draft pick would make things easier. But it’s not an absolute necessity. For the next few seasons, sit back and enjoy. It should only go up from here.