Justin De Fratus gave up the game winning hit to Kyle Blanks in the bottom of the 10th inning to drop the Philies to 36-41 on the season.
The Phillies had a commanding 3-0 lead entering the ninth inning, but Charlie Manuel made some questionable decisions that ultimately cost his team the lead.
Cliff Lee pitched a shutout through eight innings but was clearly gassed. Still, Manuel left him in the game for the ninth inning, and it proved costly.
Lee faced two hitters and failed to record an out before Manuel made the switch to Jonathan Papelbon.
The Phillies closer gave up a two-run single to Kyle Blanks.
Blanks would eventually make it to third base where he would score on a passed ball that tied the game and forced extra innings.
The Phillies threatened in the 10th, with Jimmy Rollins reaching third base with one out. Manuel elected to leave Michael Young in to face Brad Brach instead of pinch-hitting with Ryan Howard or Laynce Nix, and Young proceeded to strike out on three pitches. Domonic Brown would then fly out to center to end the threat.
Justin De Fratus would enter in the bottom of the 10th, and he clearly did not have it. Walking two batters and hitting another before giving up the game winning hit to Blanks.
For a Phillies team that has struggled all season, this was a crushing defeat and one that will surely have everyone in Philadelphia talking on Tuesday morning.
Charlie Manuel deserves a lot of the blame for the way this game ended. As he has done so many times before, Manuel left his starter go out for the ninth inning, despite looking tired.
And with Jonathan Papelbon struggling, the last thing he needed was to enter a game with the tying run coming to the plate. This was the perfect opportunity to get him a confidence-building save, and instead he was forced into another situation with no room for error.
Tonight's game was just a microcosm of the Phillies season so far: a great starting pitching effort wasted by the manager and his shaky bullpen.