Boston Red Sox: Biggest heartbreaks in franchise history

Boston Red Sox pitcher Derek Lowe reacts after walking the winning run to lose the game against the Baltimore Orioles 2-1 05 April 2001 at Camden Yards in Baltimore, MD. AFP PHOTO/HEATHER HALL (Photo by HEATHER HALL / AFP) (Photo credit should read HEATHER HALL/AFP via Getty Images)
Boston Red Sox pitcher Derek Lowe reacts after walking the winning run to lose the game against the Baltimore Orioles 2-1 05 April 2001 at Camden Yards in Baltimore, MD. AFP PHOTO/HEATHER HALL (Photo by HEATHER HALL / AFP) (Photo credit should read HEATHER HALL/AFP via Getty Images)
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OCT 1986: BOSTON RED SOX BATTER BILL BUCKNER SWINGS AT A PITCH DURING THE RED SOX 4-3 LOSS TO THE NEW YORK METS IN GAME 5 OF THE WORLD SERIES AT SHEA STADIUM IN NEW YORK, NEW YORK. Mandatory Credit: Allsport/ALLSPORT
OCT 1986: BOSTON RED SOX BATTER BILL BUCKNER SWINGS AT A PITCH DURING THE RED SOX 4-3 LOSS TO THE NEW YORK METS IN GAME 5 OF THE WORLD SERIES AT SHEA STADIUM IN NEW YORK, NEW YORK. Mandatory Credit: Allsport/ALLSPORT

Red Sox history is long and filled with memorable wins. They’ve also had their share of truly heartbreaking losses. Here’s a look at the worst of them.

Any team that’s been around as long as the Boston Red Sox have has their share of tough losses to go along with big wins. For some reason, when the Red Sox lost it was always more epic, more crushing, more devastating, more heartbreaking. Perhaps it was because of how star-crossed and dare I say it, cursed the team seemed to be between the years of 1918 and 2004.

We already looked at their greatest victories, single game, series, or otherwise in a previous article. Now it’s time to do the more difficult thing and look at the worst losses in Red Sox history. Some of these hurt at the time and still sting, while others were absolutely heartbreaking and still bother us to varying degrees even after all the Red Sox have won since 2004.

While it may seem masochistic, it’s still important to look back at these gut-punch losses in order to remember Red Sox history and all of the great players who valiantly tried to bring a World Series championship back to New England. More than that, it helps us have a deeper appreciation of what the Red Sox have done over the last twenty years.

In chronological order, let’s begin.

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