Now it's the Philadelphia Eagles' turn as the team trying to extend that misery.
The Cowboys' other two NFC East foes beat them in a division-title-or-bust showdown to close the past two regular seasons, and their hopes of avoiding the same fate Sunday night against the visiting Eagles will depend heavily on Kyle Orton instead of Romo.
"The more times you put yourself in these situations, you have to keep getting better," said Romo, 1-6 in elimination games. "You have to have a stronger belief in yourself than the doubt of other people."
Now there's no doubt Romo will be on the bench for this one. Cowboys coach Jason Garrett said Romo underwent back surgery Friday after getting hurt in last Sunday's 24-23 comeback win over Washington.
That leaves Orton starting Sunday's matchup with the winner claiming the East title and the loser failing to qualify for the playoffs. The Eagles would take the crown if there's a tie.
"We've been operating as if Kyle Orton is going to be our starting quarterback," Garrett said. "At the same time we were trying to do whatever we could to see if we could help Tony and get him back as quickly as possible. We just felt like this was the best course of action."
Romo is 0-3 in regular-season finales with the division title at stake. The first of those defeats came in Philadelphia, 44-6 in 2008. Romo had three interceptions in last year's 28-18 loss at Washington following a 31-14 defeat to the New York Giants to close the 2011 season.
That's also the last day Orton started a regular-season game - with Kansas City - and he would sign with Dallas (8-7) a few months later. He's never led a team to the postseason and hasn't started a late-season game with playoff implications since going 0-4 to close 2009 as Denver was eliminated.
"I don't think the offense changes too much with one or the other," Eagles defensive coordinator Billy Davis said. "I think we're prepared for both of them, and we're prepared to give the Dallas Cowboys the absolute best no matter who is the quarterback."
While Orton has plenty of experience - he's 35-34 in nine NFL seasons - a game of this magnitude is new territory for counterpart Nick Foles.
His worst performance of the season came against Dallas on Oct. 20 in his second game as Philadelphia's starter. Foles went 11 of 29 for 80 yards and left with a concussion at the end of the third quarter in a 17-3 loss.
"I know everybody is going to dwell on last time, but this game isn't the last game," said Foles, now the league's top-rated passer.
"If I look into every little thing that I did and try to break it down, I'll drive myself crazy as well. ... We did not play well, but from that game we've grown together as a team."
Foles would return after sitting out one game to win six of seven, and he's at 22 touchdown passes in nine starts (25 overall) with just two interceptions.
The one loss was a shocker, 48-30 to a last-place Minnesota team, but it may have come with a good lesson leading into this game - at least for the defense. Backup quarterback Matt Cassel threw for 382 yards as the Vikings became the first team in 10 games to score more than 21 points against Philadelphia despite missing injured MVP Adrian Peterson.
The Eagles (9-6) will see another veteran backup this week in Orton. Romo went 28 of 47 for 317 yards against them in Week 7.
"There are still 10 other guys out there that are going to be the same and we have to prepare for," linebacker Connor Barwin said. "Obviously, we'll watch the tape we have on Kyle Orton. He does some things differently that we'll try to prepare for, but it's still the same offense that Dallas will run. They're not going to change everything because of the quarterback the last week of the season."
Dez Bryant had eight receptions for 110 yards in the first meeting and enters this one having caught a touchdown pass in four straight games.
The absence of Romo could mean an increased workload for DeMarco Murray, who has run for 614 yards and six touchdowns over the last six games while averaging 5.8 per carry. The Eagles have held their last four opponents under 100 yards rushing.
Murray missed the first matchup with a knee injury while Dallas held LeSean McCoy to 55 yards on 18 carries. The Cowboys, though, have since given up an average of 150.6 rushing yards.
McCoy pushed his league-leading total to 1,476 rushing yards with 133 last Sunday in a 54-11 win over Chicago. He ran for two TDs and Foles threw for a pair while going 21 of 25 for 230 yards.
That game was virtually meaningless after Dallas won at Washington earlier in the day on Romo's 10-yard touchdown pass to Murray on fourth down with 1:08 to go.
Romo finished 17 of 27 for 226 yards. Orton has completed 12 of 15 passes for 129 yards in two years with Dallas.
"I think the guys have got a lot of confidence in me. I've got a lot of confidence in myself," Orton said. "I can fall back on my experience. I've played a lot of games in this league. I don't feel I have to do too much with the ball, just get it to 29 (Murray), 82 (Jason Witten) and 88 (Bryant)."