When the NFL schedule drops, everyone wants to know the same things: primetime games, division matchups, tough stretches. But often, those aren’t the games that define a team’s season. The Dallas Cowboys’ 2025 season will have four matchups that will make-or-break their year.
This year’s schedule ends with a murderer’s row. If Dallas wants those games to matter—to be a proving ground instead of a death knell—they have to capitalize on a manageable first half of the season. That means winning the games they’re supposed to win, and showing up with the same intensity each week, regardless of opponent.
These four matchups could make-or-break the Cowboys’ season.
Jan 5, 2025; Arlington, Texas, USA; Dallas Cowboys running back Deuce Vaughn (42) reacts after getting a first down against the Washington Commanders during the fourth quarter at AT&T Stadium. Mandatory Credit: Tim Heitman-Imagn Images
These Games Might Not Be Flashy, But They Could Define The Season
Dallas Can’t Afford A Letdown In Chicago
The Chicago Bears entered last season with stealth playoff hopes—an outlook that turned out to be overly optimistic. They were a mess under Matt Eberflus, who was fired midseason, and Caleb Williams never settled in behind an offensive line that gave up the most sacks of any team in the league last year.
Enter new head coach Ben Johnson, one of the brightest young offensive minds in football. Williams is expected to take a leap in Year 2, and the Bears added two new weapons in this year’s draft: tight end Colston Loveland and wide receiver Luther Burden. They’ll be at home, motivated to make an early-season statement, and looking to prove they belong in a hyper-competitive NFC North. This won’t be the same Bears team as last year.
Meanwhile, Dallas could be walking right into a trap. If they drop a tough Week 1 game at the Philadelphia Eagles, and assuming they take care of the New York Giants in Week 2, this game becomes an early pivot point. Win it, and they’re 2-1 heading into a Sunday Night Football showdown with the Green Bay Packers. Lose it, and you’re staring at the possibility of a 1–3 start—a hole that could bury the season before October.
This isn’t just about beating a team you’re supposed to beat. It’s about focus, discipline, and proving that this version of the Cowboys is capable of handling business on the road against a young, hungry team looking to make an early statement.
Dallas Has A Denver Broncos Problem
Week 8 takes the Cowboys on the road to face a problem they haven’t solved in 30 years. Dallas hasn’t beaten the Denver Broncos since 1995: they’re winless in their last seven meetings, and 4-9 all-time in the regular season against the Broncos. Add in the Sean Payton factor, and this one feels personal.
Payton will want to stick it to Dallas. He has a history with the Cowboys organization and has publicly expressed doubts about their ability to build a sustainable culture and a long-term winner. Shots fired. Now, he has a tough, physical team that made a surprise playoff run last year with a rookie quarterback and a rowdy home crowd that always creates a tough environment for visitors. If the Cowboys come into Mile High with anything less than full focus and intensity, they’ll get hit in the mouth.
This game also lands in a dangerous part of the schedule. It’s the beginning of a three-game stretch—with a bye week in between—before Dallas enters its late-season gauntlet. A win here could set the tone for a midseason run. A loss only ratchets up pressure heading into a brutal second half.
For a team with playoff expectations, this is not a game they can afford to treat like a gift-wrapped ‘W’.
The Cardinals Have the Cowboys’ Number
Inexplicably, the Cowboys struggle with the Arizona Cardinals. There’s no logical reason why, but they do. Dallas is 1-7 in their last eight matchups against Arizona, and while the rosters and coaches have changed, the results haven’t. For whatever reason, Arizona seems to bring out the worst in this team.
The Cowboys will be back home for this matchup, but that’s hardly comforting. Kyler Murray has shone at AT&T Stadium, with a pristine 9-0 record going back to his time as a star at Allen High School. Regardless of the stage, he’s always looked completely at home in Arlington.
This matchup falls right before a bye week and in between road games at Denver and Las Vegas. This game is easy to overlook, but that would be a big mistake. Arizona might not be a contender, but they play fast and loose, and Dallas has a troubling history of letting games like these slip away. In a season where every win could be the difference between a home playoff game or traveling in January, this is the kind of matchup the Cowboys have to take seriously.
Ignore the record. Forget the standings. Arizona always comes to play against Dallas, and the Cowboys need to be ready for it.
Must-Win Matchup After The Bye Week
Week 11 is a Monday Night Football showdown with the Las Vegas Raiders that could define the second half of the Cowboys’ season. They will be coming off their bye, and there’s no excuse not to be ready for this one.
The Raiders are one of the most intriguing teams in 2025. New head coach Pete Carroll is a proven winner; they traded for veteran quarterback Geno Smith, took arguably the best player in this year’s draft, and have one of the best home crowds in the NFL. After being a mess last season, Vegas now looks like a professional operation—and a prime candidate for a quick turnaround. If the Cowboys come out flat, they’ll lose.
Dallas has to win this game. Not just because it’s in primetime, but because it’s the last “winnable” game before their brutal six-game closing stretch. This game is a measuring stick that will answer a few questions: How does this team handle preparation? Focus? Pressure? A win in Vegas sets the tone for the fight ahead. A loss? Suddenly, Week 12 against Philadelphia starts to feel like a must-win just to stay afloat.
For a team trying to shed the “same ol’ Cowboys” label, this is the kind of post-bye business trip they have to handle.
The Dallas Cowboys’ 2025 Season Will Be Defined By These Games
These aren’t games that will headline NFL promo reels. They’re not vintage showdowns against San Francisco or Green Bay. But for this year’s Cowboys, they might be the most important games on their schedule.
Ideally, Dallas goes 4-0. 3-1 at worst. If they split—or worse—their season might be over before they even reach the so-called “proving ground” portion of their schedule. The margin for error in the NFC is razor-thin, and the Cowboys’ late-season slate doesn’t allow for early-season stumbles.
If this team is serious about taking the next step, they’ll prove it in these games, when the lights aren’t as bright, but the pressure is just as real.
Main Photo: [Eric Hartline] – USA Today Sports