Dallas Cowboys 2019 schedule: Ranking the 5 toughest games

Week 4 at New Orleans Saints

Last season, perhaps the biggest statement that the Cowboys made was topping the New Orleans Saints in a Thursday night matchup. With the Saints riding high and Dallas trying to prove themselves after the Amari Cooper trade, America’s Team put forth a dominant defensive effort to win, 13-10. Though it won’t be as late in the season as it was last year, a matchup against the Saints again presents the opportunity for Jason Garrett’s team to prove themselves.

Dallas starts off the 2019 season with three games they should cruise through, facing the Giants, Redskins and Dolphins to begin the year. That will then put them going on the road to face a Saints team with Super Bowl aspirations. If the Cowboys want to establish themselves early on in the year as a contender in the NFC, going on the road to New Orleans and picking up a win would certainly help that cause.

Week 16 at Philadelphia Eagles

While the Redskins and Giants are projected to be relative pushovers in the NFC East, the Eagles are decidedly not that. This is a team not far removed from winning Super Bowl LII and, with Carson Wentz hoping to be fully healthy, they have the tools to make another playoff run. Thus, it could likely come down to them and the Cowboys atop the division, which makes a Week 16 class in Philadelphia all the more juicy.

There is never any love lost between the Cowboys and Eagles, but when you add effects on the postseason to mix, things could get even more heated. This is a leave-it-all-on-the-field type of game against a division rival and, even if Philly isn’t the caliber of the Bears, Patriots, Rams and Saints, that makes this game the toughes of the 2019 season for Dallas.