Training camp is underway in Oxnard for the Cowboys. As they look to have a bounceback 2025 season, every game counts. It will be a tough year for the Boys as they are in a stacked division. They also play against two other amazing divisions in the AFC West and the NFC North. But which games on their calendar will they be circling? Here are the top 6 toughest games for the 2025 Cowboys. For a full game by game prediction for the Cowboys, see this article.
#8. Week 3 @ Chicago Bears
As always, the Bears are offseason champions. They landed the best coach in the cycle, revitalized their offensive lined, and beefed up the weapons around Caleb Williams. The Cowboys will face them early on, before injuries have taken place but after they’ve had a few weeks to work out the kinks. We know Caleb is athletic, but what can he look like when he’s protected and has a competent head coach? The Cowboys will find out in Week 3, and they’ll be lucky if they escape Chicago with a W.
#7. Week 4 vs. Green Bay Packers
The Packers and Cowboys have a history, and last time they visited Dallas it ended in disaster for the Cowboy’s season. This will be an early test for the Boys to prove if they have any chance at changing their playoff fortunes. If they can exorcise their green and yellow demons with a win over the Pack, it will be an excellent sign for their playoff chances. But if the Packers whip them at home once again, it will bring up a lot of tough questions for Dak Prescott and the whole Dallas team.
#6. Week 16 vs. Los Angeles Chargers
I’ve twice predicted that this game will be an L for the Cowboys, and I also think it will be a hard-fought battle. The Chargers have a tough, hard-nosed identity, and you know a Harbaugh-coached team will run it down your throat. The only chance the Boys have here is a high-flying passing attack between CeeDee and George Pickens being too much for LA’s young secondary. Either way, this will be a tough game late in the year with potentially extremely high stakes for both teams.
#5. Week 8 @ Denver Broncos
The Broncos are another team that massively improved in the offseason, especially on defense. They added two stars from San Francisco (a team that has given Dak trouble in the past). This is also a matchup where the head coaching difference will be very clear, especially when it comes to the Payton offense vs. the Cowboys defense. This will be a hard fought battle and the Cowboys are at a slight disadvantage at almost every position aside from QB and WR. Yet again, we will lean on Dak and the receivers for fireworks to lead us to victory.
#4. Week 17 @ Washington Commanders
We all know that Jayden Daniels is a phenomenon, and the Cowboys will be dealing with him for many years to come. This game could also have extremely high stakes, given that it could determine a playoff berth or seeding for one or both teams. And the Cowboys will be the away team and carrying all the bruises and fatigue that you normally carry by Week 17. We all know Jayden is great in the clutch, so if this comes down to the wire, we can’t like our odds. We once again have to rely on a high-flying offense to get us a lead, all while trying to contain the dynamic young QB from architecting a comeback.
#3. Week 13 vs. Kansas City Chiefs
Shocker, but when the Chiefs come to town, it’s gonna be a tough game. Mahomes and Reid are the best in the business, and the Chiefs young defense is very scary as well. If Trent McDuffie can neutralize one of our receivers, the other one will have to step up big time. And as always against Mahomes, the defense will have to be top notch to stand a chance. Thank God we don’t have to visit Arrowhead in November, but even so this will be a very tough out.
#2. Week 14 @ Detroit Lions
As was demonstrated last year, it’s clearly personal when the Lions face us. I won’t argue that the call in 2023 was a bit unfair, and that perhaps we didn’t deserve the win. But the fact remains that the Lions will be revved up to face us, and they’re an extremely talented football team. With Aidan Hutchinson and their legion of injured players on the defense returning, they will be a fearsome challenge for Dak Prescott. And Jahmyr Gibbs, Amon-Ra St.Brown, and Jameson Williams present copious challenges for our middling defense.
#1. Week 1 @ Philadelphia Eagles
No surprise here. The Eagles are our arch-rivals and things always get personal between us. Not only that, but we will be starting our season by visiting their famously hostile crowd. Not to mention, they’ll be celebrating their banner raising and starting their title defense. This will be an absolutely brutal way for the Cowboys to start their season and prove their mettle against their tough division rival. This is one of the toughest and best game on our schedule, and a sensational way to open the 2025 season.
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