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5 worst matchups on Cowboys 2023 schedule

These Cowboys games project as the toughest for Dallas in the upcoming regular season.

NFL: NFC Divisional Round-Dallas Cowboys at San Francisco 49ers Kyle Terada-USA TODAY Sports

We finally have the NFL’s full 2023 regular season schedule. As it’s being vigorously dissected throughout sports media right now, one of the key angles is where the toughest matchups fall for every team. Here are what project to be the five biggest challenges on the Dallas Cowboys’ 2023 schedule.

Granted, these projections are based solely on present information, and the assumption of full health for the opposing team. We fully acknowledge that a missing quarterback or some other unforeseen issue could dramatically alter the difficulty level of these games.

But for the moment, with what we know today, here are the most worrisome matchups for the Cowboys this year:

Week 1 - @ New York Giants (SNF)

The G-Men are on the rise, coming off their first winning season since 2016. While the Cowboys have gone 11-1 against them over the last six years, including 2-0 last year, New York is a much more concerning opponent under Bruce Daboll’s leadership than the recent series of failed coaches.

Having to open the season in primetime, on the road, against a division rival who’s retained key talent and added upgrades this offseason; it all adds up to a tough night for the Cowboys. You can’t lean on Dallas’ dominance over the Giants these last several years. Even last season’s wins were only by a touchdown.

What’s more, the Cowboys will be going into the season opener with a revised offensive system under Mike McCarthy and Brian Schottenheimer. While that could lead to new wrinkles that New York isn’t prepared for, it also gives the Giants a potential edge in coaching continuity as they’re bringing back the same coordinators from last year.

Week 5 - @ San Francisco 49ers (SNF)

This one would’ve made the list regardless of where it fell on the schedule. But throw in a primetime slot and that just worsens matters for the visiting Cowboys.

Believe it or not, Dallas actually has a winning record over the 49ers since 2016. They’ve gone 3-0 against them in the regular season since Dak Prescott became the starting quarterback.

The fear factor for this year is the last two meetings, both playoff eliminations at the hands of San Francisco. While neither was hardly a blowout, the 49ers have simply overpowered and outclassed the Cowboys recently and felt like the glass ceiling toward legitimate contender status. Hopefully, Dallas will finally break through.

Week 6 - @ Los Angeles Chargers (MNF)

If this had been a random Sunday afternoon matchup it might have been trumped by a couple of other games. But the timing of this visit to Los Angeles is brutal for the Cowboys.

It’s bad enough that Dallas has back-to-back road games in California, facing the Niners the week before. But to make matters worse, the Chargers will be coming off an early Week 5 bye ahead of this matchup. They get a week to tweak things after the first quarter of the season, then get a home game.

Those are just the breaks with every year’s schedule; it’s not possible to have constant equity with so many x-factors to deal with. But with the Chargers also a rising team coming off a 10-7 season, they didn’t need any more help for this rare meeting with Dallas.

Week 9 - @ Philadelphia Eagles (SNF)

Of course, right? This is the marquee matchup for both teams as they prepare to collide for the rivalry, the division crown, and hopefully loftier goals in 2023. Unfortunately, the first meeting has to be on the Eagles’ turf and in a primetime game.

I promise that I’m not biased against night games, by the way. It’s more coincidental than anything; these games would be nearly as rough if they were on a Sunday after church. But there’s no denying that the bright lights of primetime bring added pressure.

With any two-game series as we have with our division rivals each year, you’d prefer the first one be at home. It gives you that edge and a win helps take some of the pressure off the second meeting. A loss to a division rival in the first game, especially one you expect to be in a two-horse race with, can be a huge blow with lingering effects for the remainder of the season.

Week 15 - @ Buffalo Bills

Thankfully, this one will be on a Sunday afternoon. That’s less about the primetime pressure and just the hope that it will be a warmer day in Buffalo. This mid-December meeting with our old pals from the 90s has the potential to be a frosty reunion.

Colder weather favors toughness and fundamental football. Hopefully, adding DT Mazi Smith in the draft will improve Dallas’ run defense and overall grit in the trenches. It will also be a big test for their decisions on the offensive line, especially whether or Tyron Smith is still standing upright this late into the season.

But regardless of the weather or even the location, this is a huge test against one of the NFL’s elite teams in recent years. The Bills have had 10-13 victories in each of the last four years. They just might be the toughest opponent on the schedule on pure talent, and these other factors only add to the Cowboys’ challenge.

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