Dak Prescott gave Cowboys fans and Cowboys haters alike a fresh reminder of just how long it’s been since Dallas reached the Super Bowl.
As the team arrived at its training camp hotel, Prescott was wearing a Super Bowl XXX shirt - the one tied to Dallas’ last trip to the title game. Super Bowl XXX was played on Jan. 28, 1996, when the Cowboys beat the Steelers 27-17. That was the franchise’s last Super Bowl appearance.
The shirt turned into an accidental billboard for the gap between that era and the one Dallas is still living in now. Since that last Super Bowl win, the Cowboys have gone 258-226-1 in the regular season, a solid mark that hasn’t carried over once the playoffs begin. In the postseason over that stretch, Dallas is 5-13.
That means five playoff wins in thirty years. The Eagles, by comparison, have 20 playoff wins in that same span, including 6 since 2022 and 4 postseason wins in 2024 alone.
And the Cowboys’ playoff misery hasn’t just been about numbers. They haven’t reached the NFC Championship Game since 1996, and they’re 0-7 in the Divisional Round. The list of brutal exits is long: the 2023 Wild Card loss to the 7-seed Packers, when Dallas fell behind 27-0 in the first half; the 2021 Wild Card game against San Francisco, when Dak ran up the middle with 14 seconds left and no timeouts before the game ended without a spike; and Tony Romo’s infamous fumbled field goal snap in the 2006 Wild Card.
Then there was last season, when the Cowboys finished 7-9-1 and missed the playoffs entirely.
So yes, Prescott’s shirt did more than just catch attention. It dragged three decades of Cowboys frustration right back into the spotlight.
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