Just under two weeks stand between the Dallas Cowboys and the start of the 2026 regular season. After two disappointing seasons in which they missed the playoffs both years, offseason upgrades have given Dallas high hopes for this upcoming season.
If the Cowboys are going to return to the postseason, they’ll need to take care of business in a few swing games on their difficult regular-season schedule. Here are three must-win games for the Cowboys this upcoming season.
1) Week 2 vs Washington Commanders
It may seem a bit crazy to list
a Week 2 matchup as a must-win, but this game absolutely falls into that category for the Cowboys. Dallas opens up the season with two divisional matchups in a row, traveling to New York to take on the Giants in Week 1 before returning home to host the Commanders.
While Dallas has dominated the rivalry with the Giants in recent memory, this matchup will be much more difficult than years past. New York undoubtedly got better this offseason, and emotions will be running high as John Harbaugh makes his debut as the team’s new head coach. Dallas is favored and very well could win the game, but there is a real possibility they walk out of New York 0-1.
If that happens, the Week 2 matchup against the Commanders becomes a clear must-win. Dropping to 0-2 with both losses coming to division opponents could nearly sink your season two weeks in. Even if the Cowboys beat the Giants to kick off the season, this matchup still carries plenty of weight. In that scenario, being able to go to 2-0 with two divisional wins would give Dallas a huge leg up in the division race early on.
2) Week 9 at Indianapolis Colts
While a non-conference matchup in Week 9 may not figure to carry much weight, the positioning of this game in Dallas’ schedule makes it very important. After traveling to Green Bay and Philadelphia in back-to-back weeks, Dallas will face the Cardinals, Colts, 49ers, and Titans in weeks eight through eleven.
If the Cowboys want any shot at making the playoffs, the games against the Cardinals and Titans should be easy wins. The 49ers will be, without a doubt, the toughest opponent of the four, and with their recent history against San Francisco, it’s easy to see Dallas dropping this one. That leaves the swing game at Indy in Week 9.
With such a tough schedule to start the year, the Cowboys may need to make up some ground in their five November games. This matchup against the Colts will likely be the difference between Dallas going 3-1 or 2-2 during the easiest part of their schedule.
Indianapolis’ rushing attack will make this a tough game, but if Dallas comes out with a win, it could be huge for their playoff hopes.
3) Week 17 vs New York Giants
All things considered, it’s hard to see a world where the Cowboys make the playoffs without winning this Week 17 matchup against the Giants. It’s unclear just where the Giants will be in their re-build at this point in the season. Winning this game could be the deciding factor if Dallas wins the NFC East or makes the postseason in some capacity.
If the Cowboys are in the playoff hunt at all, this home matchup against a divisional opponent in the second-to-last week of the regular season will carry tons of weight. Dallas needs to walk away with a win in this matchup no matter what.
