Damon, who played for both the Yanks and BoSox during his 18-year career, told TMZ Sports on Thursday he's rooting for the Yankees and expects the playoff upset.
"New York's my team," he said. "The Yankees, that's who I want to win."
The Yanks scored a 7-2 victory over the Oakland Athletics in the AL Wild Card Game on Wednesday night to earn a place in the ALDS opposite the longtime rival Red Sox.
They are +140 underdogs (bet $100 to win $140) heading into the series, per OddsShark. Boston is a -160 favorite (bet $160 to win $100) after posting an MLB-best 108-54 regular-season record. New York went 100-62.
Damon told TMZ he believes the short best-of-five series will benefit the Yankees, however, and he thinks the pressure is firmly on Boston's shoulders.
"If the Red Sox don't win [the World Series], it's a failed season," he said.
The Sox hold a slight edge in both runs scored (876-851, the top two totals in MLB) and team ERA (3.75-3.78).
The hyped ALDS matchup starts Friday night at Fenway Park in Boston.