Boston Red Sox: Most memorable games in franchise history

Red Sox win 1999 ALDS behind Pedro Martinez & Troy O’Leary

This win didn’t result in a pennant, World Series, or individual record, but it was a huge win nonetheless. After going to the World Series in 1986 and losing in the ALCS in 1988 and 1990, the Red Sox had made two more trips to the postseason but hadn’t advanced past the ALDS, losing in 1995 and 1998.

In 1999, things looked like they were finally lining up correctly for the Red Sox. Their ace Pedro Martinez was coming off of one of the most dominating seasons in baseball history and shortstop Nomar Garciaparra‘s incredible season led things on the offensive side. With Martinez pitching Game One, it looked like Boston would make short work of the Indians and move on to the ALCS.

Instead, Pedro left that game in the fifth inning with a shoulder injury and the Indians took a 2-0 series lead before the Red Sox came back to tie the series and force a decisive game five. Tied 8-8 going into the bottom of the fourth inning, Pedro was put into the game in relief and proceeded to throw six no-hit innings while completely shutting the Indians down.

While Pedro took care of the Indians, Troy O’Leary put the Red Sox up for good with a go-ahead three-run homer in the seventh inning. That hit came after his grand slam in the third inning which kept the Sox in the game before Pedro came in. Behind Pedro’s mastery and O’Leary’s 7 RBI game, the Red Sox completed the comeback and won the series to move on to the ALCS.

While they ended up losing to the dynastic Yankees in five games in the ALCS, the Red Sox showed real grit in finally breaking through to make the final round of the American League playoffs for the first time since 1990. It would be another five years before they’d finally break through, conquer the Yankees, and win another pennant, but for those of us who were around at the time it cannot be overstated how big this win was.