Expert predictions for Cowboys-Buccaneers: Can Dallas end its losing streak vs. Tom Brady?

The Cowboys will look to grab their first road playoff win since the 1992 season.

The Cowboys (12-5) are set to start the playoffs on the road, meeting the Brady-led Buccaneers in the wild card round Monday night at Raymond James Stadium in Tampa, Fla. At this point, Dallas is all too familiar with the Bucs after dropping the last two meetings against the Florida-based foe.

Tampa Bay (8-9) comes into the matchup motivated by an NFC South division title and big plays from its veteran signal caller. Brady owns a 7-0 mark against the Cowboys, with the most recent victory taking place at AT&T Stadium to open the 2022-23 season.

Can Dallas finally get past Brady to keep its Super Bowl hopes alive? Will Brady embark on another extended playoff run?

Our panel of columnists, beat writers and special contributors make predictions for the matchup below.

Tim Cowlishaw

In their 0-7 stretch against Tom Brady that goes back 20 years, the Cowboys have to have more than “they’re due” on their side in order to end it Monday. And I believe they will. Brady does not get sacked much but he can be hurried into interceptions. In four games during the month of December while we were all wondering about Dak’s errant throws, Brady threw seven of them. Cowboys must win the turnover battle — and a team that led the NFL in takeaways is capable of that — to finish the Brady streak and advance.

Cowboys 23, Bucs 16

Michael Gehlken

I cannot recall a time in my career when I’ve heard so many players praise a game plan as the Cowboys have this week. What all that locker-room confidence means exactly, we’ll see. But the team mentality seems to be in a far healthier place than at this point last year.

Cowboys 27, Bucs 24

Damon Marx

The Cowboys limped to the finish line with a sputtering offense and leaky secondary. The Tampa Bay offense scuffled throughout the entire season. So this should be an even matchup and a back-and-forth game. Yet, if it comes down to making a play during crunch time, which quarterback would you choose to deliver: Tom Brady or Dak Prescott? That’s what I thought.

Bucs 23, Cowboys 17

David Moore

Chances are you have no clue that Tom Brady has never lost to the Cowboys. Oh, wait, you do? You say that’s why you’re so fatalistic heading into this Wild Card matchup even though Dallas won four more games during the regular season than Tampa Bay and is the more talented team across the board. Until the Cowboys beat Brady, you won’t allow yourself to think it can happen? That’s fair. Enjoy the game.

Cowboys 27, Bucs 21

Kevin Sherrington

The good news: The Cowboys had a great walkthrough Wednesday. Really. A bad week of practices last week led to a bad game against the Commanders, so, by that reasoning, they should play great against the Bucs. I’m not buying it. This team has been going the wrong way for weeks. Nearly time to update the organizational chart.

Bucs 27, Cowboys 21

Jean-Jacques Taylor

The Cowboys’ most important player, Dak Prescott, is playing his worst football of the season heading into the playoffs. The running game has disappeared and the left cornerback spot has the potential to be a disaster. The Cowboys are the better team and they’re more talented, but it ain’t my job to have hope, faith and optimism. I’m an admitted prisoner of the moment, so I’m taking Brady over Dak.

Bucs 23, Cowboys 19

Calvin Watkins

The Cowboys haven’t won a road playoff game since the 1992 season. The players of this current group said it’s got nothing to do with them. Well, if they’re not getting the running game going, Dallas will be at home next weekend. We believe in the defense. DeMarcus Lawrence and Micah Parsons will have a sack party. This game will be ugly but it’s OK if you win.

Cowboys 20, Bucs 17


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