1999: AL wild card champions
The Red Sox made their deepest postseason run since 1986 in the ’99 season, finishing second in the AL East but winning the wild card. Pedro Martinez went 23-4 with a 2.07 ERA and won the AL Cy Young award.
The Sox faced the Cleveland Indians in the ALDS, and fell behind 2-0. The Sox rallied though, coming back to tie the series at two games apiece and force a deciding Game 5. The Sox fell behind 5-2 after two innings and 8-7 after three, but came back and took the lead, winning the game and the series in improbable fashion.
It was their first postseason series win since 1986. The Sox then faced the Yankees in the ALCS and lost the first two games by just one run each. Game 3 was a different story and included Martinez matched up against Roger Clemens, who was making his first postseason appearance in Fenway Park since leaving the club three years earlier and then signing with the hated Yankees.
The Red Sox clobbered Clemens, scoring six runs off him in the first three innings and sending him off early. The Sox won the game 13-1, but that would be the only win of the series for Boston, as the Yankees took Games 4 and 5 to win the pennant.