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Ranking all 16 Cowboys games this season by difficulty

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Which Cowboys games are going to be the most difficult in 2019?

NFL: New England Patriots at Dallas Cowboys Erich Schlegel-USA TODAY Sports

This upcoming season will be a tough one for the Dallas Cowboys. It will be tough because, well, the games are going to be difficult, but it will also be challenging because everyone is going to talk about the franchise’s recent inability to put together consecutive seasons of note.

In 2019 the Cowboys have the dreaded “first-place schedule” thanks to winning the NFC East last season. The reality is that this idea is mostly a myth, two games can make a difference but teams change so much year-to-year so you never know.

What is true, though, is that the Cowboys happen to have drawn some of the better teams from last season in their upcoming campaign. In 2019, the Cowboys will play six games against teams that made the playoffs last season, three of those contests occur in their last four games.

What’s more is that the Cowboys not only have to play against teams that were in the postseason a year ago, they also have to take on both teams that appeared in Super Bowl LIII (and subsequently, obviously, the reigning world champions). That’s tough cookies.

Which games are going to be the most difficult this season for the Cowboys? Tony Casillas and I kicked this can around on the latest episode of The 75O (subscribe to all BTB podcasts here) and put together our lists. Here’s mine.


Games 16-13: Dolphins, Giants, at Giants, Lions

We’re counting down here so we’ll start with the four least difficult games for the Cowboys:

  • Number 16: Miami Dolphins
  • Number 15: New York Giants
  • Number 14: @ New York Giants
  • Number 13: @ Detroit Lions

This might seem like more playful ribbing of the G-Men, but it’s just hard to see that team being competitive this season. Obviously a game on the road is more difficult than one at home in theory which is why the home contest is slotted further back. Only the Miami Dolphins look to be an easier matchup, and thankfully that will occur in Week 3.

In reality, the Cowboys open their season with three really favorable games (NYG, at WASH, MIA). They’re going to need a cushion because things get far more difficult rather quickly, but having two of your easier games out of the first three weeks is quite the way to get going.

It stands to reason that the Lions could be better in 2019, but Matthew Stafford is just so hard to predict. Last year the Cowboys just barely beat Detroit, but that was before the arrival of Amari Cooper. I think Dallas should do better this year.


Games 12-9: Redskins, Bills, Vikings, at Jets

This is where things (obviously) get a little more difficult. Washington at home ranked this low isn’t meant to disrespect them but the reality of it is that that game occurs in Week 17. It’s so hard to know if it will even mean anything, and historic trend suggests it won’t.

  • Number 12: Washington Redskins
  • Number 11: Buffalo Bills (Thanksgiving)
  • Number 10: Minnesota Vikings
  • Number 9: @ New York Jets

Buffalo will be an interesting Thanksgiving Day game and the Cole Beasley factor will certainly make it a lot more fun. The reality though is that their quarterback is so suspect and the rest of their offense is quite stagnant. Minnesota is a wholly good Kirk Cousins away from being a legitimate contender in the conference, but the likelihood of getting such a rarity is in fact low.

If I’m being honest I might be sleeping a bit on Minnesota, but this is a quarterback league which is why these games are ranked the way they are. Cousins has yet to prove his whole worth as the Vikings signal-caller, and the rest of the quarterbacks associated with these teams aren’t exactly worth bragging about either (Washington remains a question mark though). Plus that game is at home which makes it just a bit easier.

The game in Washington just edges out the game in New York for me because, well, the Cowboys lost that one last season. We don’t know who the Redskins are going to be, but their defense is underrated and the whole “you throw records out during division contests” narrative does exist for a reason.

It will be fascinating to watch how Le’Veon Bell performs against the Hot Boyz, though.


Games 8-5: at Redskins, Packers, Eagles, at Bears

As mentioned, the game in Washington won’t exactly be easy, but the three that come ahead of on this list are definitely going to be difficult.

  • Number 8: @ Washington Redskins
  • Number 7: Green Bay Packers
  • Number 6: Philadelphia Eagles
  • Number 5: @ Chicago Bears

Color me optimistic, but I think this is the year that the Cowboys finally take care of business at home against the Green Bay Packers (every blind squirrel, right?). It just feels like a new era with Green Bay having a new coach and what not, it’s hard to see Davante Adams breaking our hearts again.

Besides, the games against Philadelphia and in Chicago are likely going to be far more difficult for the Cowboys. The Eagles and Bears will be physical matchups and the latter will be on the road in December... in Chicago. Yikes.

The only thing keeping that Eagles game as low as six is that it’s at home. Oh, and the fact that there are four really hard games left. That, too.


Games 4-1: Rams, at Saints, at Eagles, at Patriots

It’s pretty wild that a matchup against the team that knocked the Cowboys out of the playoffs last season comes in at fourth, but to be fair it’s slotted as the most difficult home game. There are a lot of people anticipating a step back from Los Angeles in 2019, but they should be respected nonetheless.

It definitely helps things that the game in the Big Easy for the Cowboys is earlier in the season, something about the Superdome in double digit weeks of it makes it feel harder. What keeps Philadelphia ahead of them is that it is such a hostile environment that just so happens to be the home of a division rival. One the Cowboys have been battling with for the last few years.

There’s no question as to which game is the most difficult of the season for the Cowboys and it’s the one against the reigning Super Bowl Champions. Playing in New England around the time of year where it’s just getting chilly (November 24th, the Sunday before Thanksgiving) has all the feelings of something epic and heartbreaking.

If you close your eyes (don’t because then you won’t be able to read this) you can practically see it. It’ll get dark by the third quarter, Jim Nantz and Tony Romo will be on the call, and things will be tight all throughout the second half. The Cowboys will be showing that they can hang with the Patriots but there will be a looming feeling of uneasiness.

Hopefully the team is capable of fighting that feeling off and getting a huge win, a victory in New England would be quite the statement. Especially considering this is the hardest game of the season.