Boston Red Sox: Biggest heartbreaks in franchise history

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.