Tom Brady’s quest for an eighth Super Bowl ring begins on Monday night, when his Tampa Bay Buccaneers host Dak Prescott and the Dallas Cowboys to conclude Wild Card Weekend of the NFL Playoffs. 

Brady’s Bucs (8-9) got in by way of NFC South division title, while the Cowboys (12-5) were relegated to wild card status and must hit the road despite a record four games better. Tampa shut down Dallas 19-3 in a season-opener; Prescott broke his thumb in that game. 

Dallas, which had won six of seven before a head-scratching blowout loss to Washington in Week 18, is favored by 2.5 points on the road in the latest Cowboys vs. Buccaneers odds on NFL betting sites. The Over/Under is set at 45.5 points. 

Bookies.com NFL handicapper Adam Thompson – focused on hitting over 60% of his NFL picks for a fourth-consecutive season – reveals his NFL betting picks and props for the important rematch. 

RELATED: Vikings vs. Giants Wild Card Picks + Best Bets

Cowboys vs. Buccaneers Point Spread Pick

A lot of bettors are expecting Tom Brady and the Bucs to rise to the occasion and for Dak Prescott and the Cowboys to falter now that it’s the postseason. But why? Tampa Bay has been the worst covering team not just this year but in the last six years, and Brady has a horrible primetime track record. 

Tampa isn’t one to be able to take advantage of Dallas’ top weakness, that being Dak Prescott’s questionable decision-making at times. The advantage on the line and Dallas’ ability to rattle QBs, plus an exponentially better run game, gives Dallas the edge on the road. Lock in the Cowboys before it gets to a field goal. 

Up to $1,500 in Bonus Bets if Your First Bet Loses Promo Code: BOOKIES

Tap for Promo Activated! Visit site

Used 9 Times Today

Bonus Bets Expire in 7 Days. One New Customer Offer Only. Must be 21+ to participate & present in OH. In partnership with MGM Northfield Park. Gambling problem? Call 1-800-GAMBLER. Visit BetMGM.com for T&Cs. US promotional offers not available in NY, NV, or Puerto Rico.

Cowboys vs. Buccaneers Over/Under Best Bet

We’ll forget last week’s 26-6 dud against the Commanders last week. Only one other time in nearly two months had a Cowboys game total finished under 50 points. They’ve scored 34-plus five times in the second half of the season. Tampa Bay allows 23 ppg at home, ranking 26th. 

The Bucs’ offense generates more scoring at home, though only 21.1 ppg. But 20-24 points sounds right, and when compared to the 27-30 I expect the Cowboys to put up, that gives us the Over. We like the spread more than the total, but the Over is the preferred spot. 

$1,000 First Bet on Caesars

Tap for Promo Activated! Visit site

Used 9 Times Today

OH only. 21+. New users and first wager only. Must register with eligible promo code. Bet amount of qualifying wager returned only if wager is settled as a loss. Maximum bet credit $1,000; must be used within 14 days of receipt. See Caesars.com/promos for full terms. Void where prohibited. Know When To Stop Before You Start.® Gambling problem? Call 1-800-GAMBLER

Cowboys vs. Buccaneers Moneyline Pick

Dallas is -140 on the moneyline, and we like the Boys to cover at -2.5 so it stands to reason that we expect a win as well. Tampa Bay is +120 – not a bad price for Tom Brady in the postseason. Brady has never lost to the Cowboys in seven career games. 

The Bucs were only 1-4 at home vs. playoff-level teams, the lone victory against barely-qualified Seattle. No team with a losing record has ever won a playoff game. Dallas to win is the way to go on betting sites. 

Up to $1,500 in Bonus Bets if Your First Bet Loses Promo Code: BOOKIES

Tap for Promo Activated! Visit site

Used 8 Times Today

Bonus Bets Expire in 7 Days. One New Customer Offer Only. Must be 21+ to participate & present in OH. In partnership with MGM Northfield Park. Gambling problem? Call 1-800-GAMBLER. Visit BetMGM.com for T&Cs. US promotional offers not available in NY, NV, or Puerto Rico.

Best Cowboys vs. Buccaneers Player Props

Mike Evans, Over 64.5 Receiving Yards

Odds: -110 at BetMGM

Brady is going to sling it no matter what. I’d be surprised if Todd Bowles doesn’t call 50 pass plays. The more pass plays, the more Mike Evans, who had 10 catches for 207 yards in a Week 17 playoff-clincher vs. the Panthers. That said, Evans piles up way more stats in losses than he does wins. Expect Brady lean on his top target in the postseason. 

Michael Gallup, Under 36.5 Receiving Yards

Odds: -110 at DraftKings

Gallup hasn’t registered 40 receiving yards in four straight weeks and only five times all season (over 50 yards just once). The Buccaneers rank No. 10 vs. the and have been especially good at limiting No. 2 wideouts. Dallas’ focus will be on the run game, and with Dalton Schultz emerging in the pass attack, Gallup isn’t likely to have a breakout Monday night here. 

$1,000 First Bet on Caesars

Tap for Promo Activated! Visit site

Used 50 Times Today

OH only. 21+. New users and first wager only. Must register with eligible promo code. Bet amount of qualifying wager returned only if wager is settled as a loss. Maximum bet credit $1,000; must be used within 14 days of receipt. See Caesars.com/promos for full terms. Void where prohibited. Know When To Stop Before You Start.® Gambling problem? Call 1-800-GAMBLER