Dallas Cowboys 2019-20 NFL Postseason - Odds and Predictions

Written by: Mike Lukas
Updated October 14, 2022
11 min read

The fate of the 2019-20 Dallas Cowboys’ upcoming season is apparently coming down to what most NFL preseason contract situations are caused by – money, mainly because three of the franchise’s hottest playmakers are either up for new deals soon or wish they were.

No doubt owner and general (and micro) manager Jerry Jones has it all under control – he usually seems to – and by the time these Cowboys face the New York Giants on September 8 in Week 1, the billionaire’s roster will contain the best possible players he can afford.

Though the Cowboys won the NFC East in 2018, they are not expected (at least by the odds makers) to do the same this season, so we take a look at the odds and predictions of quarterback Dak Prescott’s (and America’s) team from Dallas making it to the NFL postseason this year.

The 2019 Dallas Cowboys are:

  • Owner: Jerry Jones
  • General Manager: Jerry Jones
  • Head Coach: Jason Garrett (Promoted November 2010)
  • Offensive Coordinator: Kellen Moore (Promoted January 2019)
  • Defensive Coordinator: Rod Marinelli (Promoted January 2014)
  • Quarterback: Dak Prescott (4th NFL season, all with Cowboys)
  • Offensive Stars: Running back Ezekiel Elliott and Wide Receiver Amari Cooper
  • Defensive Stars: Linebacker Leighton Vander Esch and End Demarcus Lawrence

How did the Dallas Cowboys do in 2018?

For the first time since 2002, the Dallas Cowboys did not have tight end Jason Witten in the lineup (he had retired and was making a living in the Monday Night Football booth), and the Cowboys ended up in first place of the NFC East, posting a 10-6 record and earning a spot in the postseason after failing to do so the prior season.

The Cowboys started out the 2018 season on a lousy 3-5 run but then caught fire (thanks to much needed help from their mid-season trade for wide receiver Amari Cooper) and closed out the second half of the season with a stellar 7-1 record.

The season ended at the Divisional Playoffs when the Los Angeles Rams beat them by a score of 30-22, but it was an impressive season nonetheless, especially for quarterback Dak Prescott, who passed for a career high 3,885 yards, and running back Ezekiel Elliott, who put up 2,001 total yards from scrimmage with 9 touchdowns.

What major offseason moves happened in Dallas?

There was quite a bit of NFL traffic heading in and out of the Dallas organization this offseason, the biggest name coming in belonging to Jason Witten, the future Hall-of-Fame tight end, who hung up his Monday Night Football microphone and returned to the field once again.

Also added to the Cowboys’ roster was wide receiver Randall Cobb, who signed a one-year deal worth $2 million after playing in nine games last season for the Green Bay Packers and catching 38 balls for 383 yards and 2 touchdowns.

Leaving the franchise this offseason (among others) was free agent wide receiver Cole Beasley, who signed a four-year deal with the Buffalo Bills worth $29 million, making 2019 the first year since 2011 that he will not be on the Cowboys’ roster to start the season.

What is happening with Ezekiel Elliott’s contract?

At this time, the Cowboys have reportedly made offers to running back Ezekiel Elliott, quarterback Dak Prescott and wide receiver Amari Cooper that would put each of them in the top five for their position, but none of them have yet to sign.

In fact, Elliott, a third-year player who is under contract until 2020, has been refusing to show up to any offseason workouts or to training camp, and has even threatened to miss regular season games if he doesn’t get a new contract, though skipping paychecks (and bumping his current contract back a year) is not something he is likely to do.

Unlike with running back Le’Veon Bell, who sat out his third franchise tag last season so he could become a free agent, Elliott is still under contract and would gain nothing by skipping the season but would lose a whole lot of money if he did.

Owner Jones is said to be confident that “it’ll happen” when it comes to Elliott, Prescott and Cooper, so fans will have to just be patient and wait out the necessary dance that must take place before NFL players are rightly paid.

What is going on with Dak Prescott’s contract?

Supposedly, owner and general manager Jerry Jones offered quarterback Dak Prescott a contract extension worth about $30 million a year, which would have made him one of the top five best paid quarterbacks, but Prescott said no.

That has to do with the market in general, and more specifically the fact that the Seattle Seahawks’ Russell Wilson just pulled in a historic $140 million four-year deal and the Philadelphia Eagles’ Carson Wentz just got a $128 million four-year contract extension.

Where Prescott deserves to fit in all of that is up to his agent and Jones to decide, but chances are it will all get done before Week 1 in September.

What is the latest on Amari Cooper’s contract?

Wide receiver Amari Cooper, whom the Cowboys’ signed mid-season last year, is in the fifth and final year of his current rookie contract and will make $13.9 million in 2019.

Cooper came in and gave the Cowboys’ offense a huge boost starting in Week 8 when he caught 53 balls for 725 yards and 6 touchdowns for the year, averaging 80.6 yards per game and earning his third Pro Bowl selection in four NFL seasons.

Reportedly, Cooper’s demands are “shockingly high” so it remains to be seen if the Cowboys will be able to retain this talented receivers’ services past 2019.

When was the last time the Cowboys made the playoffs?

That would be last season when the 10-6 Cowboys were beaten in the Divisional Round by the eventual Super Bowl runner-ups, the Los Angeles Rams, by a score of 30-22.

The Dallas Cowboys have made the postseason four times in the last decade (2009, 2014, 2016 and 2018), and lost in the Divisional Playoffs in all four of those years.

The Cowboys are still considered America’s team after having won five total Super Bowl wins (out of eight appearances) in the history of the franchise, though it’s been awhile since their last Lombardi Trophy, which they earned in 1995 against the Pittsburgh Steelers in Super Bowl XXX by the score of 27-17.

Why WILL the Cowboys make it to the postseason in 2019?

Anyone who watched the Dallas Cowboys in the second half of last season knows that this team was clicking and on fire, and given that they are essentially the same roster this year, it stands to reason they will start the season exactly where they left off.

Especially given that minus Cole Beasley but plus Randall Cobb they haven’t changed, but more importantly they are now plus Jason Witten, a player destined for the NFL Hall of Fame who adds veteran expertise in the locker room and sharp routes and soft hands on the gridiron.

Once Elliott and Prescott get paid (and they will), there is no doubt as to how much they can contribute, and if they can lead this Cowboys’ offense to even higher levels (and Demarcus Lawrence and Leighton Vander Esch can continue leading a defense ranked 7th last season), Dallas is certainly destined for another playoff appearance, at the very least as a Wild Card.

Why WON’T the Cowboys make it to the postseason in 2019?

Even if the Dallas Cowboys play as good or better than they did last season, there are a lot of NFC teams who are set up to do even better, namely the Philadelphia Eagles, Minnesota Vikings, Green Bay Packers and the Seattle Seahawks, to name a few.

Point is, not only will it be difficult for the Cowboys to win the NFC East again (it’s not just that the Eagles look terrific, even the New York Giants look tougher), earning a Wild Card spot will be more difficult this season with all the rising competition in the conference.

There’s no way Witten is as good now as he used to be, so to count on him making a difference after sitting out a year is expecting a lot from him.

And there’s no way even Jones can make all three of his superstars financially happy, so expect there to be a drop in someone’s numbers as a result, and having that kind of disappointment inside of the locker room will be enough to bring the entire team down.

What are the current odds and predictions for the Dallas Cowboys’ 2019 NFL postseason?

According to the odds makers, the 2019-20 Dallas Cowboys are predicted to come in second place in the NFC East (first place apparently goes to the Philadelphia Eagles), but regardless, Dallas is expected to play in the postseason as a Wild Card team.

Next, we look at some of the odds and predictions of the 2019-20 Dallas Cowboys postseason chances and briefly analyze each.

Will the Dallas Cowboys make the NFL postseason in 2019?

Sportsbook YES NO Link
888Sport NJ +110 -134

* 21+ | NJ only | If you or someone you know has a gambling problem, call 1-800-GAMBLER

Analysis: The Cowboys made it to the postseason last year for the third time in five seasons and they continue to be an NFC threat.

However, odds makers don’t seem to agree, and they are making the ‘no postseason’ bet the favorite here.

Tough to bet against Dallas not playing in January.

Odds of the Cowboys winning the NFC East:

Sportsbook Cowboys NFC East Win Cowboys NFC East 2nd Cowboys NFC East 3rd Cowboys NFC East 4th Link
888Sport NJ +160 +115 +500 +1100

* 21+ | NJ only | If you or someone you know has a gambling problem, call 1-800-GAMBLER

Analysis: Looks like the Dallas Cowboys are predicted by the odds makers to finish second in the NFC East to the Philadelphia Eagles.

The odds of the Cowboys finishing in first aren’t much worse, though.

Tough to bet on the Eagles being better with Wentz always getting injured, but it’s even tougher counting on the Cowboys to win their division, something they’ve only done four times in the last decade.

Number of regular season Cowboys games won:

Sportsbook Over 9 Under 9 Link
888Sport NJ +110 -134

* 21+ | NJ only | If you or someone you know has a gambling problem, call 1-800-GAMBLER

Analysis: The Cowboys would have won the over on this bet just four times out of the last ten seasons.

Dallas is tied for the fourteenth most difficult schedule this season, so they should be able to make a decent run and win at least ten games.

Of course, that assumes happy superstars with solid contracts, so it’s anyone’s guess how well that smoke will clear or if it will get in the way of double-digit wins.

Odds of the Cowboys winning the NFC Championship:

Sportsbook NFC Championship Link
888Sport NJ +1200

* 21+ | NJ only | If you or someone you know has a gambling problem, call 1-800-GAMBLER

Analysis: You bet $100 here and you could win $1200 back (plus your investment) but this is a tough one this season.

Even if the Cowboys do make it to the playoffs and past the first round, there are five other NFC teams that have better odds of winning the Conference Championship than they have, so Dallas will be fighting an uphill postseason battle no matter how they get in.

Of course, these Cowboys are due, so you diehard fans might want to put money down just in case this is finally their year (again).

Odds of the Cowboys winning Super Bowl LIV:

Sportsbook NFL Championship Winner Link
888Sport NJ +2500

* 21+ | NJ only | If you or someone you know has a gambling problem, call 1-800-GAMBLER

Analysis: When it comes to winning this next Super Bowl, eleven other NFL teams have better odds than Dallas does.

But with the Prescott-Cooper connection back on the field, with future Hall-of-Famer and freshly head-shaved Jason Witten back on the roster and with running back (and fully paid?) Ezekiel Elliott finally happy, the Cowboys could make a run at the Super Bowl.

Sure, a lot of things would have to happen first, but another Lombardi Trophy for Jerry Jones and company is never out of the question until their very last snap.

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Mike Lukas

Sports Betting & Gambling Industry Analyst

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Mike Lukas is a retired standup comedian turned freelance writer now living in Dallas, Texas, originally from Cleveland, Ohio. His love for the game of football and all things Cleveland Browns turned Mike into a pro blogger years ago. Now Mike enjoys writing about all thirty-two NFL teams, hoping to help football gamblers gain a slight edge in their pursuit of the perfect wager.
Nationality: American
Education: N/A
Favourite Sportsbook: bet365 Sportsbook
Favourite Casino: Caesars Palace Casino
23 years
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