The Boston Celtics had an opportunity to end the city’s gruel title drought of almost four years, but they came up short in the NBA Finals. Losing Game 6 to the visiting Golden State Warriors, the team ended the series with a 2-4 record.

Losing on a game’s biggest stage is always tough, and the Celtics’ NBA counterparts know a thing or two about it. The New England Patriots may be tied for most Super Bowl wins with six, but they also came up on the wrong end in five championship games.

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So, the share some of the Celtics’ heartbreak let’s take a look at the Patriots’ Super Bowl losses and rank them from least to most bad.

5. Super Bowl XX vs. Chicago Bears

The Patriots’ first ever appearance on the big stage was a disaster. Going up against one of the best teams in NFL history the team suffered what was at the time the worst title game loss of the NFL’s Super Bowl era: led by quarterback Tony Eason, who went 0-for-6 and was sacked three times before getting benched in favor of Steve Grogan, the team lost 46-10.

New England never stood a chance against the Bears. The team was out-gained 123 to 408, turned the ball over six times and surrendered seven sacks. While it did manage to score the first points of the postseason against Chicago’s mighty 46-defense defense, it was not nearly enough.

Why is that game not higher up on the list, though? There is one simple reason: the 1985 Patriots were a Cinderella story through and through, with few if any people giving them a shot to even make it that far. They had not won a playoff game in 22 years, going all the way back to the old AFL, and just reaching the Super Bowl was a success. So, if you have to rank a game fifth out of five this is it.

4. Super Bowl XXXI vs. Green Bay Packers

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It took the Patriots 11 years to return to the Super Bowl after their loss to the Bears, and once again they entered the game as major underdogs: the oddsmakers had listed the Packers as 14-point favorites. They eventually lived up to the pre-game expectations, winning 35-21 to drop New England to 0-2 in the Super Bowl.

New England’s second Super Bowl appearance was a more competitive contest than its first, but the team’s turnovers and inability to prevent big plays were too much to overcome. As a result, the team came up short in what would turn out to be head coach Bill Parcells’ final game on the sidelines.

3. Super Bowl LII vs. Philadelphia Eagles

The Patriots’ 2017 season came to a disappointing end against the underdog Eagles. Tom Brady put up a historic performance, throwing for a Super Bowl record 505 yards as well as three touchdowns, while Danny Amendola, Chris Hogan and Rob Gronkowski all crossed the 100-yard receiving barrier.

New England’s offense was not perfect against a talented Philadelphia defense, but it did its job — something that cannot be said of the defense. With starting cornerback Malcolm Butler benched and Mr. February himself, Dont’a Hightower, absent, the unit forced just one punt all game and surrendered 41 total points and 538 yards. For comparison, the Patriots managed to score just 33 despite gaining 613 yards of offense.

The Patriots had their chances to win the game, but bad play at inopportune times and a costly turnover on the game’s lone sack sealed the deal.

2. Super Bowl XLVI vs. New York Giants

Four years after losing the perfect season to the Giants, the Patriots had a chance at redemption. Unfortunately, the result was the same as it was in Super Bowl XLII: New York coming away victoriously in what was a highly contested game.

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Despite the Patriots’ early miscues — including a safety and a defensive penalty negating a takeaway — they were able to put themselves in a good position in the third quarter. Up 17-9, however, the offense began to stall: it was unable to put up any more points over the final 26 minutes of the game and missed potentially game-sealing plays late in the fourth quarter.

This, in turn, allowed the Giants to take a late 21-17 lead to beat New England for a second time on the game’s biggest stage. The Patriots were out for revenge, instead they suffered more heartbreak at the hands of Eli Manning and company.

1. Super Bowl XLII vs. New York Giants

The aforementioned first Super Bowl meeting with the Giants ended with one of the most prominent upsets in NFL history. The Patriots, after all, entered the game with a perfect 18-0 record and as the first ever team to go through a 16-game regular season undefeated — a slate that included a 38-35 win over the Giants just five weeks earlier.

Super Bowl LII, however, played out differently. New England’s record-breaking offense struggled to hit its stride until late in the fourth quarter, when it took a 14-10 lead with 2:45 left to go. All that was needed to complete the greatest season the league has ever seen was the Patriots defense stopping the Giants from driving 83 yards.

The unit had multiple chances to do so, but came up short every time: New York converted a 4th-and-1; Asante Samuel was unable to come down with a game-sealing interception; Eli Manning escaped a sack on third down to complete a miraculous 32-yard pass to David Tyree. Four plays later, the Giants were up 17-14 with only 30 seconds left.

The Patriots still had a chance to fight back, but Corey Webster made the play of his life to break up a 60-yard bomb to Randy Moss. And thus, New England lost its first Super Bowl of the Brady-Belichick era in the most excruciating of ways: the team had perfection in its grasp and several opportunities to seal the deal within the final three minutes. However, the 2007 Patriots simply ran out of gas when it mattered most.

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