Cowboys vs. Giants Rewind: 5 unforgettable Tony Romo vs. Eli Manning matchups

Happy New Year. I hope your 2026 is off to a good start.

Just one game remains in the Dallas Cowboys‘ 2025 season, as they travel to the Big Apple to take on the New York Giants before both teams begin the 2026 offseason.

In this article, let’s take you back in time in this historic rivalry and revisit one of the most entertaining eras of these two NFC East teams.

Some Sundays, a Cowboys and Giants matchup didn’t feel like a regular season game, it felt like a stress test.

You’d get a lead, lose it, get it back, then spend the final three minutes bracing for something ridiculous.

More often than not, the chaos had two names attached to it: Tony Romo and Eli Manning.

They met 17 times, and the endings were rarely clean. Comebacks, breakdowns, two-minute drills, and a playoff gut punch, this rivalry had a little bit of everything.

Here are the five games that captured what Romo vs. Manning was all about.

Honorable Mention: Week 13, 2006 Romo to Witten

Romo’s first time as the Cowboys’ starter occurred mid way through 2006, and gave fans plenty to cheer about, but his first taste of the Giants came on Monday Night Football, a rough night that ended in three interceptions and a 36-22 loss.

Six weeks later, in the rematch at Giants Stadium, the game played out far differently.

Manning threw for 270 yards and two touchdowns, and New York had plenty of chances to bury Dallas, but mistakes piled up. The Giants committed four personal foul penalties, coughed up a costly fumble, and struggled to finish in the red zone.

Still, Manning delivered late, leading a 63-yard drive capped by a 7-yard touchdown to Plaxico Burress. And here’s the part that mattered: on that possession, the Giants used a timeout that preserved roughly 40 extra seconds.

Romo didn’t need much time at all.

He hit a young Jason Witten for a 42-yard gain, setting up Martin Gramatica for the game-winner as Dallas escaped with a 23-20 win.

A classic early chapter in what became a rivalry defined by late-game nerves.

5) Week 12, 2014: Cowboys win, but a Giant star is born

By late November of 2014, Dallas was sitting atop the NFC East and trying to stack up more wins, while the Giants were already playing spoiler. The game itself had that familiar Giants-Cowboys feel, big plays, momentum swings, and just enough chaos to make it memorable.

New York controlled the first half, going into the break up 21-10. But Dallas flipped the script after halftime. Romo sparked the comeback with a 45-yard touchdown to Cole Beasley, then later connected with Dez Bryant on a 31-yard score to give the Cowboys a 24-21 lead.

Of course, it didn’t stay that way.

Manning answered with a 14-play, 93-yard touchdown drive late in the fourth to put the Giants back ahead. And once again, Romo had a response ready, driving Dallas 80 yards in seven plays, finishing with a 13-yard touchdown to Bryant to pull out the win.

However, everyone remembers that night for Odell Beckham Jr.’s catch, one of the most famous plays in league history.

The other truth is this, in a game that felt like it was slipping away twice, Romo steadied the whole thing and got Dallas out of there.

4) Week 1, 2015: A Giant miscue hands Dallas a steal

If you watched this one live, it felt… off. Sloppy pace. Weird rhythm. The Cowboys’ offense didn’t look sharp, and turnovers kept showing up at the worst times.

Dallas trailed by double digits twice, 16-6 in the third quarter and 23-13 in the fourth, but kept hanging around. Then the game reached the moment where the Giants basically had it wrapped up.

With New York up 23-20 late and inside the goal line, the Giants didn’t need to do anything fancy. Run the ball. Force Dallas to burn time. Even if you don’t score, you make the Cowboys operate with no timeouts and almost no clock.

Instead, on a 3rd-and-goal play, Manning threw the ball out of the end zone rather than going down, and it left 1:37 on the clock.

That was the opening, and Romo kicked the door in.

Dallas went six plays in 1:27, and after Romo secured a poor snap, he found Witten for the 11-yard game-winning touchdown. Final: Cowboys 27, Giants 26.

It ended up being the final Romo vs. Manning matchup, and it was fitting, a game decided by one late mistake and one calm, efficient drive.

3) Week 14, 2011: Manning magic in full effect

The NFC East was a mess in 2011, which meant every big December matchup felt like it carried double weight. The Giants came to Arlington spiraling, losers of four straight after a 6-2 start.

The Cowboys were 7-5 and leading the division.

It played out like a rivalry game usually does: back-and-forth scoring and late-game stress.

Dallas looked like it had finally landed the knockout when Romo hit Dez Bryant for a 50-yard touchdown to go up 34-22 with under six minutes left. But the Giants didn’t fold. Manning Magic went into full two-minute surgeon mode.

First: an 80-yard drive ending with a touchdown pass to Jake Ballard.

Then came a brutal swing: on the Cowboys’ next possession, Romo recognized the blitz on 3rd-and-5, signaled to Miles Austin, and took a shot, but the ball sailed on him.

Manning got it back and did it again, driving New York 53 yards in six plays, finishing with a Brandon Jacobs touchdown. The Giants hit the two-point conversion to take a 37-34 lead.

Romo still managed to put Dallas in position for a game-tying kick: Dan Bailey from 47 yards.

Bailey made it… and then Giants coach Tom Coughlin iced him. On the re-kick, Jason Pierre-Paul broke through and blocked it.

Game over. Giants 37, Cowboys 34.

If you want a single game that captures “Manning can’t possibly keep getting away with this,” this was it.

2) Week 2, 2009: Welcome to Jerry World

The first-ever regular season game at what was then called Cowboys Stadium (a.k.a. Jerry World) had to be dramatic.

The football gods weren’t going to let it be anything else.

On September 20, 2009, the 1-0 Giants and 1-0 Cowboys met in front of 105,121 fans, and both quarterbacks put on a show.

Manning won the stat battle, 330 yards and two touchdowns, but the bigger story was how wild the entire game felt.

This one had everything: multiple lead changes, 805 total yards, 42 combined first downs, seven touchdowns, four field goals, and even a bizarre moment where a ball hit the cleat of Jason Witten, leading to an interception by Kenny Phillips. Because of course it did.

Dallas turned it over four times, including a Romo pick-six, and somehow still had a chance to win late, which honestly feels like the most Giants-Cowboys thing imaginable.

Romo still scored twice himself, a 1-yard touchdown pass to Witten and a 3-yard rushing touchdown, and Dallas led by one with under four minutes left.

But in the defining moment, Manning took the Giants on an 11-play, 57-yard drive, setting up Lawrence Tynes for the 37-yard game-winning field goal. Final: Giants 33, Cowboys 31.

That was the rivalry at its peak: messy, dramatic, and decided by who got the ball last.

1) 2008 NFC Divisional Round: The upset that still stings

No game in this rivalry carried more weight than this one.

Dallas was 13-3, stacked with talent, and coming off a season where Romo threw a then-franchise record 36 touchdowns. The Cowboys had swept the Giants in the regular season and were expected to roll into the NFC Championship Game for the first time since 1995.

Instead, it became one Giant upset.

The Giants struck first, with Manning hitting Amani Toomer for a 52-yard touchdown on the opening drive. Dallas responded with scores from Marion Barber and Terrell Owens to take a 14-7 lead, and with the Cowboys controlling the second quarter, it looked like they were settling in.

Then Manning flipped it fast.

In the final stretch of the half, he led a quick touchdown drive, a seven-play burst that took 46 seconds, ending with another Toomer touchdown to make it 14-14 at the break.

The second half turned into a trench fight, and New York’s pass rush, led by Michael Strahan, made life miserable for Romo. The Giants took the lead in the fourth on a Brandon Jacobs 1-yard touchdown, and Dallas had one last shot late.

On 4th-and-11, Romo’s pass was picked off in the end zone by R.W. McQuarters, sealing a 21-17 Giants win.

It’s remembered not just as an upset, but as the turning point of the Giants’ run to a Super Bowl title, and one of the most painful playoff endings of the Romo era.

And yes, Romo and Witten never returned to Cabo before a playoff game after that one.