The 10 Worst Days in Boston Sports History

While Boston sports teams have recently turned their losing ways around and have won six championships this century, throughout the years, our teams have had an almost infinite amount of heartbreaking days.

In fact, there have been so many that the recent OT game seven Bruin loss, and Celtics' choking in game six on the same night could not even break the top ten. Here are the ones that did.

10. May 10, 1979

The Bruins had come behind in the series (3-2) against the Canadiens, and held the lead in game seven, thanks to a Rick Middleton goal with four minutes remaining.

However, their Stanley Cup Finals hopes were dashed after Guy Lafleur tie it up on a power play goal (too many men on the ice), and Yvon Lambert won the series in overtime. The Candiens went on to crush the Rangers in five. The Bruins haven't won a Cup since.

9. January 26, 1986

There is losing, and there is getting crushed. The 1986 Patriots expemplified what it meant to be crushed when they played the Chicago Bears in the Super Bowl.

The Patriots were held to negative 19 yards in the first half, they had 123 total yards at the end of the game (second lowest in Super Bowl history), with only seven earned on the ground (still a Super Bowl record). The Bears also set a record for number of sacks in Super Bowl with seven. While it was not the most depressing day in Boston Sports, it may very well have been the most embarrassing.

8. June 19, 1986

This was the single worst day for the Boston Celtics franchise. Just 48 hours after selecting the uber-talented Len Bias with the second pick in the NBA Draft, he died from a cardiac arrhythmia caused by cocaine.

Many believed that Bias had the talent to challenge the Bulls during the Jordan era, if he had lived. After losing in the Finals the next year, the Celts did not make it back to the finals for 21 years.

7. October 15, 1946

The Red Sox found themselves in their first World Series since 1918. After winning game five, they only needed one win to claim victory. In game six, the Sox could only manage one run and lost 4-1. In game seven, the Sox were able to tie the game up at three in the top of the eighth. But, they allowed the winning run to score in the bottom of the inning on a supposedly botched relay by second baseman Johnny Pesky.

6. October 2, 1978

1978 provided one of the most horrible seasons in the history of Red Sox. They were ahead of the Yankees by 14 games in July, but the Yankees battled back and forced a one game tie-breaker.

The Sox looked as though they would make it to the postseason after all, leading 4-1 in the seventh. Then, Bucky "****ing" Dent came to the plate and hit a pop-up that continued floating over Yaz, and the Green Monster, to tie the game. Reggie Jackson provided the game-winning run in the eighth on a solo home run.

5. October 22, 1975

While game six often overshadows game seven, the fact is that, the Reds still won the series. The Sox were seven outs away from winning their first championship in 57 years. However, Griffey tied it up on a Pete Rose single, and scored again in the ninth to win it.

4. February 3, 2008

The Patriots had done the impossible, they had gone 16-0 in the regular season and won their first two playoff games. The only thing between them and the perfect season were the underdog, "happy to be there" Giants.

This was unlike all of the other horrible days that Boston has been through, because, this time, the Patriots were supposed to win. They had everything. They were supposed to wipe the floor with the Giants.

Instead, the Giants hung in during the first three quarters, and completely dismantled the Pats offense. The Giants even took the lead (10-7) with 11 minutes left. However, the Patriots looked as though they had avoided the upset when Moss caught a Brady pass for a touchdown—with only 2:42 left on the clock.

But, the Giants marched down the field, with Eli Manning playing so well that I personally wanted a DNA test to prove that it wasn't Peyton. After the Eli scramble, and the Tyree helmet catch, I knew it was not going the end well, and sure enough, Burress caught the game-winning touchdown with 35 seconds left.

3. October 25, 1986

While Buckner is usually blamed for the game six loss in the 1986 World Series, it was entirely a team effort that blew this game for the Sox. Bill Buckner didn't have a prayer at beating Wilson to the bag, since Stanley chose to not cover first.

The largest part of the blame must go to Manager John McNamara. Not only did he leave Buckner in the game, but he also allowed rookie Mike Greenwell to pinch-hit for Clemens in the eighth, with a runner in scoring position, instead of Baylor. And don't even get me started on Schiraldi.

2. December 26, 1919

The most well-known trade in baseball history, and probably all of sports, came a day after Christmas in 1919, a year after the Red Sox won their third championship in four years.

Frazee, the Red Sox owner, needed money to finance two things—a broadway play, known as My Lady Friends (later changed to No No Nanette), and to buy Fenway Park, which he had previously been renting. The White Sox offered superstar outfielder "Shoeless" Joe Jackson and $60,000, but the Yankees offered more money ($100,000), and Frazee took it.

The deal soldified the Red Sox financially, and allowed the Frazee to go ahead with his other business ventures. But, what happened over the next 86 years changed the landscape of Boston sports forever.

1. October 16, 2003

Logically, this day should not be No. 1, since it was only an ALCS series, and not the World Series or Super Bowl. But for whatever reason, this is the one that always gets me.

When the Sox led 4-0 in the fourth and chased Clemens out of the game, it was the first time that I actually thought that we were going to do it. I had a right to be confident. In the bottom of the seventh, Boston was up by three runs and Pedro, the man that I had never seen give up three runs in an inning, was on the mound.

But, sure enough, that's exactly what he did, and the Yankees tied it up. Then came Rivera, who completely shut them down for three innings. As the game prolonged, my gut started to feel worse and worse, until Boone nailed one of Wake's knucklers that doesn't knuckle into the upper deck, as I flung my remote through my television screen.