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Tom Brady started 41 playoff games in 20 years with the New England Patriots. And he sure did win a lot of them. In fact, Brady started his career by winning 10 consecutive postseason battles before suffering his first defeat.

While the Patriots captured six Super Bowl titles with Brady behind center, they also suffered some heartbreaking losses in postseason play. As Patriot Nation turns the page on the most successful chapter of NFL history, let’s take a look at the worst playoff losses in Brady’s time in New England.

2009 AFC Wild Card Game – Ravens run over Patriots at Gillette Stadium

Heading into this first-round matchup, Brady had lost just three playoff games. Of course, one of them came on the biggest stage (we’ll get to that later). Playing host to a physical Baltimore Ravens team led by second-year quarterback Joe Flacco, New England fans got treated to one of the worst losses in Patriots history.

Ray Rice opened the game with an 83-yard touchdown that set the stage for a lopsided defeat. Baltimore pounded the Pats on the ground and took a commanding 24-0 lead in the first quarter. Brady did throw two touchdowns, but New England never recovered from the first-quarter onslaught.

The Ravens racked up 234 rushing yards and four TD. Flacco only had to throw 10 passes (New England intercepted one of them). Brady threw three picks, took three sacks and lost a fumble. Overall, it ranked as one of the worst home losses in Brady’s 20-year career.

Super Bowl LII – Eagles win 41-33 despite Tom Brady’s record-setting night

Talk about a strange game. From Malcolm Butler spending all but one snap on the bench to controversial replays to the Philly Special, Super Bowl LII had every dramatic element possible. The Eagles entered the game as underdogs but emerged as champions.

Nick Foles played the game of his life, throwing for 373 yards and three touchdowns while also hauling in a touchdown catch on the famous trick play. Lost in the story was an all-time effort from Brady. He set the Super Bowl record with 505 passing yards. New England never punted. Yet, they still came up short largely due to a poor defensive game plan headlined by Butler’s benching. The loss definitely goes down as one of the most painful defeats in Brady’s career and definitely caused a rift between Bill Belichick and his star QB.

2015 AFC Championship – Broncos pummel Tom Brady in two-point win

Coming off an epic Super Bowl win against Seattle, New England returned to the AFC Championship in 2015. Unfortunately, injuries sapped the offense of some of its most critical players. By the time the Patriots took the field against the Broncos, the injured reserve list included: LeGarrette Blount, James Develin, Dominique Easley, Ryan Wendell, Jerod Mayo, Dion Lewis and Nate Solder.

The losses up front proved to be detrimental. Denver’s championship defense completely overwhelmed New England’s offensive line to the tune of four sacks and 17 quarterback hits. Even with a limited cast of weapons, Brady still threw for 310 yards and a touchdown, and the Pats could have forced overtime if Brady had found Rob Gronkowski in the back of the end zone on a two-point conversion.

2006 AFC Championship – Patriots blow 15-point lead to Peyton Manning

The Patriots almost never blew halftime leads during the Brady era. So when New England went to the locker room up 15 against Indianapolis, another Super Bowl trip appeared wrapped up. Then, Peyton Manning took over.

Brady’s second career playoff defeat came at the hands of the quarterback many believed to be his superior. Manning and the Colts dropped 32 points on Belichick’s defense, including 17 in the fourth quarter alone. Brady and the Patriots put up just 13 after the half, including two fourth-quarter field goals. Of course, the most memorable part of the heartbreaking loss was Reche Caldwell dropping two passes that could have set the Patriots up for a go-ahead touchdown.

Super Bowl XLII – The Helmet Catch ruins perfect Patriots season

Oh what could have been. For diehard Patriot Nation members, this game represents a painful moment in history. Brady and the Patriots entered the game with a pristine 18-0 record. Throwing to the unstoppable tandem of Randy Moss and Wes Welker, Brady set the NFL regular-season touchdown record. And don’t forget about New England’s veteran defense that featured a number of perennial Pro Bowlers: Richard Seymour, Tedy Bruschi, Mike Vrabel, Asante Samuel and Rodney Harrison.

Despite a stacked lineup, the Patriots simply didn’t deliver on the most important stage. The Giants unleashed a ferocious pass rush led by Michael Strahan and Justin Tuck. New York held the best offense in NFL history to just 14 points. And with one fateful David Tyree catch, the Patriots lost the first Super Bowl of the Tom Brady era in devastating fashion.