What’s the most heartbreaking loss for Boston teams in the last 40 years?

The city of Boston has certainly had its share of championship parades and rolling rallies over the past 40 years. However, there have also been losses that still have fans playing the “what ifs” and “should have had that one” games.

Here’s a look at 10 of the biggest “gut-wrenching losses” in Boston sports history since the ’80s. Read ’em and weep, then scroll down to vote in our poll for which one was the worst or most painful for Boston fans. Voting ends at midnight on Thursday, July 25. We’ll announce the winning loss on Friday.

Super Bowl XLII – New York Giants 17, New England Patriots 14

The game was played on February 3, 2008 at the University of Phoenix Stadium in Glendale, Arizona. Despite New England having a historic undefeated season and being heavy favorites going into the game, the Giants defeated the Patriots by a score of 17–14.

Super Bowl XLVI – New York Giants 21, New England Patriots 17

For the second time in four years, the Patriots were denied the Lombardi Trophy by Eli Manning and the New York Giants. The game was played on February 5, 2012 at Lucas Oil Stadium in Indianapolis, marking the first time the Super Bowl was played in Indiana.

2008 ALCS Game 7 – Tampa Bay Rays 4, Boston Red Sox 3

Matt Garza outhit Jon Lester for the win, while rookie David Price struck out three in 1 1/3 innings in relief for the win. Red Sox Hall of Famer Dustin Pedroia thought the 2008 Red Sox were better than the 2007 team that won the World Series.

2003 ALCS Game 7 – New York Yankees 4, Boston Red Sox 3

At Yankee Stadium, Aaron Boone’s solo home run off Tim Wakefield in the 11th inning sent the Yankees to the World Series and the Red Sox home for the winter. The game was started by Pedro Martinez and former Red Sox ace Roger Clemens. Boston led 5-2 until the bottom of the eighth inning, but Sox manager Grady Little elected to keep Martinez in the game in the eighth. The Yankees scored three runs in the inning, sending the game into extra innings.

2023 NHL Eastern Conference Finals Game 7 – Florida 4, Boston 3

The Bruins led 3–2 in the final period, but the Panthers tied the game on a goal by Brandon Montour with 59 seconds left and went on to win the game in overtime. Boston had won the Presidents Trophy for the NHL’s best regular-season record, and set NHL records for wins (65) and points (135), but were eliminated in embarrassing fashion in the first round of the playoffs.

Super Bowl LII – Philadelphia Eagles 41, New England Patriots 33

Despite Tom Brady throwing for three touchdowns and 505 yards, the Patriots, who benched defensive back Malcolm Butler after activating him before the game, were unable to stop Eagle QB Nick Foles. Foles threw for 373 yards and three touchdowns, and also caught a one-yard touchdown. The game was played on February 4, 2018 at U.S. Bank Stadium in Minneapolis.

2010 NBA Finals Game 7 – Los Angeles Lakers 83, Boston Celtics 79

The Lakers outscored the Celtics by eight points in the fourth quarter and celebrated with a four-point championship win on their home court, the Staples Center in Los Angeles.

1986 World Series Game 6 – New York Mets 6, Boston Red Sox 5

The Red Sox, still battling The Curse of the Bambino, were one strike away from an elusive World Series championship when the Mets scored two runs in the 10th inning. After making the first two outs of the inning, Red Sox reliever Calvin Schiraldi allowed consecutive hits to Gary Carter, Kevin Mitchell and Ray Knight, who was trailing 0-and-2 in the count. Red Sox manager John McNamara called up Bob Stanley to face Mookie Wilson. A wild pitch scored Mitchell with the tying run, and then a ground ball down the first base line eluded Bill Buckner and Knight raced home with the winning run, forcing a seventh and deciding game, which the Mets won 8–5.

2019 NHL Stanley Cup Finals – Game 7 – St. Louis Blues 4, Boston Bruins 1

At TD Garden, St. Louis rookie goalie Jordan Binnington made 32 saves, allowing only one goal from Matt Grzelyck. The Bruins won two of the first three games of the series, St. Louis won the next two and Boston forced a deciding game with a 5-1 victory in Game 6.

2023 NBA Eastern Conference Finals Game 7 – Miami Heat 103, Boston Celtics 84

Jayson Tatum injured his ankle in the opening minute of the game and was never the same in his 42 minutes of action, scoring just 14 points. The Heat, the Eastern Conference No. 8 seed, eventually lost to Denver in the NBA Finals.