Dallas Cowboys Playoff Hopes Hinge on Crucial 3-Game Stretch

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Bold black NFL action during a Dallas Cowboys vs. Philadelphia Eagles football game with quarterback Dak Prescott preparing to throw the football on the field.

The Dallas Cowboys are riding high after Monday night’s 33-16 win over the Raiders and rightfully so.

Dak Prescott was on fire, as was George Pickens, and Quinnen WIlliams had a great debut.

Quinnen Williams made an impressive debut for the Cowboys

But the next two weeks will ultimately decide the Cowboys’ fate. Can they make a storybook run for the playoffs?

Or will they start getting ready for the 2026 season a month early?

12 Days, 3 Big Games: The Cowboys’ Crucial Run Against the Eagles, Chiefs & Lions

Right now, not only is Philadelphia the NFC East leader, they hold the top seed in the NFC playoff picture at 8-2.

The Eagles have survived two tough battles with the Packers and the Lions. Both were one-score victories and low-scoring games, but still two huge wins.

Philadelphia beat Dallas to open the season, despite losing their best defensive lineman before the first snap of the game.

Cowboys tie up Eagles in NFC East chase

Jalen Carter will play on Sunday. But the Eagles will be without their Pro Bowl right tackle Lane Johnson.

Dallas will need to exploit that weakness, and contain Saquon Barkley, to earn a win.

Four days later they drew the always dangerous Kansas City Chiefs.

The Chiefs clearly aren’t the same team this year that made annual trips to the AFC Championship game an almost certainty.

However, they still have Patrick Mahomes at quarterback and Andy Reid as their head coach. But the Cowboys cannot expect to beat them as easily as they did Las Vegas.

The gauntlet ends on Dec. 4th in Detroit and a Lions team that crushed Dallas at AT&T Stadium last year, 47-9.

They will be a tough out on the road.

To remain in the playoff hunt, Dallas almost has to win two of these three games to get to 6-6-1. They should be able to go 3-1 down the stretch against the Vikings, Chargers, Commanders, and Giants.

Even at 9-7-1, the Cowboys would probably still need help to get into the playoffs, but they’d have a shot.

But a 1-2 run, or 0-3, over the next two calendar weeks, and the Cowboys’ playoff hopes are likely DOA at either 5-7-1 or 4-8-1.

Areas of Concern for the Cowboys Ahead of Their Playoff Push

Dallas looked good in every aspect of the game on Monday night. The offense put up 33 points and probably could have made it 40 if needed.

The defense held the Raiders in check.

Las Vegas scored nine points when the game was still in question and never generated a rushing attack.

Dallas Cowboys football team celebrating during a game, wearing white and blue uniforms, with focus on team camaraderie and player unity, in a packed stadium.

But there are reasons not to overstate the victory. Starting with who Dallas beat.

The Raiders appear to be tanking, falling to 2-8 with the loss.

Do not be surprised to see Las Vegas drafting Geno Smith’s immediate replacement in April.

Chip Kelly’s days as the Raiders offensive coordinator may also be numbered. Coming into a game against a team that can’t stop the run, Kelly called 28 passes and just four run plays in the first half.

The defensive pass coverage and tackling was nearly non-existent.

It was almost as if Las Vegas did everything they could to hand the win to the Cowboys.

Cowboys Still Winless Against Winning Teams — Can That Change in This Playoff Race?

Dallas will play four opponents with records at .500 or better over the next five weeks. The Cowboys record this year against teams .500 or better?

0-4-1 and that should give everyone in Cowboys Nation the jitters.

All four of Dallas’ wins have come against teams with losing records, and they don’t get one of those until Dec. 14th, when they host the currently 4-6 Vikings.

Kansas City is 5-5 today. The Chiefs host the 8-2 Colts on Sunday and could be below .500 when they arrive in Dallas on Thanksgiving Day.

Richard Paolinelli

Richard Paolinelli

Richard Paolinelli is a sports journalist and author. In addition to his work at InsideTheStar.com, he has a Substack -- Dispatches From A SciFi Scribe – where he discusses numerous topics, including sports in general. He started his newspaper career in 1991 with the Gallup (NM) Independent before going to the Modesto (CA) Bee, Gustine (CA) Press-Standard, and Turlock (CA) Journal -- where he won the 2001 Best Sports Story, in the annual California Newspaper Publishers Association’s Better Newspapers Contest. He then moved to the Merced (CA) Sun-Star, Tracy (CA) Press, Patch and finished his career in 2011 with the San Francisco (CA) Examiner. He has written two Non-Fiction sports books, 11 novels, and has over 30 published short stories.

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