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3 Biggest Must-Win Games on the Cowboys' 2023 Schedule

Divisional matchups are always big, but only one makes the list of the Cowboys' top three must-win games in 2023.
Jason Schandl
Jason Schandl

Sport DFW

3 must-win games on the Cowboys' schedule in 2023, including a Week 5 clash with the San Francisco 49ers. / Kyle Terada-USA TODAY Sports

Is it dramatic to deem a single regular season game a must-win before the season even gets started? Maybe, but with just a 17-game regular season it's really hard to overstate how much importance a single win can carry.

And we all know that wins and losses aren't all created equal. Only the most delusional fans think their team will go 17-0, so there are some games on the schedule that fans won't be too worried about losing. The better your team, however, the fewer of those spots you can afford to have.

And the Dallas Cowboys are vying to be the best team in the 2023-24 season. This is a squad with legitimate Super Bowl aspirations, and it's not just Cowboys fans saying it. The betting markets fully agree, ranking Dallas No. 6 in the NFL (and No. 3 in the NFC) in Super Bowl odds.

Just about every other legitimate contender in the NFC is on the Cowboys' schedule this season, which means plenty of tough tests and the need to rack up a few wins over that top competition.

With that in mind, here are three games that Dallas absolutely cannot afford to lose in the 2023-24 campaign.

1. Week 5 @ San Francisco 49ers

You might think an early-season matchup against a fellow favorite in the NFC is one of those games I mentioned above that wouldn't be a crushing loss, but that's not the case here.

Every returning Cowboys player is going to have this one circled with revenge on their mind, and it's important that we prove last year's Divisional Round result was nothing more than a fluke.

Taking on the 49ers early in the season gives Dallas a tremendous opportunity. San Francisco is a team that's expected to be in contention but could very well get off to a slow start before rounding into form later in the year.

Whether it's Brock Purdy returning from his torn UCL or Trey Lance trying to prove that he's a legit NFL starter, the Niners offense has a lot to prove and a lot to figure out early in the season.

Considering we may be competing with San Francisco for a first-round bye in the playoffs when all is said and done, holding the tiebreaker with a head-to-head win could prove crucial.

2. Week 17 vs. Detroit Lions

They may not have made the playoffs last year, but the Detroit Lions were obviously becoming a force to be reckoned with by the end of the regular season. As for the year ahead, they're one of the top threats to win the entire NFC.

As I talked about with the 49ers, one factor that makes this game a must-win is that it's a potential tiebreaker for the No. 1 seed in the NFC and a first-round bye in the playoffs. That's obviously a huge edge, both in terms of recovery time for potentially injured players and in how much easier it is to win three playoff games than four.

Even if we're not duking it out for a potential tiebreaker, a Week 17 win or loss has the potential to cause massive shakeups in the playoff seeding regardless of where the Cowboys stand.

This will also be a potential breath of fresh air during a really tough part of the schedule, as Dallas returns home for this one after back-to-back road games against Buffalo and Miami.

It's hard to love the timing (Saturday night on December 30), but this game is a pivotal one all the same.

3. Week 14 vs. Philadelphia Eagles

This will be the second Cowboys-Eagles game of the year, and there are a few reasons why winning this one is even more important than the Week 9 meeting in Philly.

For starters, that road game at Lincoln Financial Field may be the absolute toughest spot on the Dallas schedule this season. The Eagles are the favorites to win the whole NFC, and playing them in Philly is about as hard as it gets. I mentioned in the intro that you can excuse a loss or two on the schedule, and that first game is one of those spots where you can't get too upset at an L.

But Week 14 is different. This game is in Dallas, and what we absolutely can't afford to do is drop the season series 0-2 to any team in the NFC East. Week 14 is also getting much closer to playoff time.

By Week 14 these teams will look a lot more like the postseason versions of themselves. Team chemistry will be built and injuries will be racking up. It's not just about building momentum with a win late in the postseason, but about proving that the most up-to-date version of the Cowboys is the team to beat in the NFC East down the stretch, and potentially stealing back a seeding tiebreaker while we're at it.

This one's on Sunday Night Football, and you can expect it to have the atmosphere of a playoff game.


Game odds refresh periodically and are subject to change,.

Jason Schandl

Jason Schandl

Since getting his start in the fantasy sports and betting space in 2016, Jason has spent years covering every major sport and a wide variety of teams across each league. When he's not staying on top of the latest sports news, you can find Jason outside camping or at home with his cats.