Walk-offs in the postseason are something special, but walk-offs against the Boston Red Sox have a completely different dynamic. On a late October night in 1999, Bernie Williams provided the latter moment to put the Yanks up 1-0 in that year’s ALCS.
1999 ALCS Game 1 - October 13
Final Score: Yankees 4, Red Sox 3
Game MVP: Orlando Hernández
Looking back at it now, that 1999 ALCS is the one with the least drama out of the three that the Yanks played with the Red Sox from then to 2004, but despite the 4-1 win, this matchup could have gone very differently.