"We asked a lot of a lot of people," manager Terry Francona said. "You get into extra innings, and we had our chances, and we couldn't shove a run across so we could go to [Jonathan Papelbon]."
There was a chance in the 11th inning, when the Sox had runners on first and third before David Ortiz grounded into a double play.
There was a chance in the 10th inning, when Rays reliever Trever Miller issued walks to Kevin Youkilis and Jed Lowrie, but ex-Ray Julio Lugo hit into a double play.
But the biggest missed opportunity came during regulation, in the ninth inning.
After Kevin Cash hit a leadoff single, Dustin Pedroia reached on a fielder's choice, and Cash avoided the tag at second, putting the Sox in a prime position to take the lead. But Rays closer Dan Wheeler hunkered down to retire heavyweights Ortiz and Manny Ramirez for the inning's final two outs.
"This was a tough one," Cash said. "I mean, [Thursday night's loss to the Angels] was really tough. I thought if we had pulled that one out, that would have pulled for a really strong homestand and we would bounce back [again] today.
"We had our opportunities [tonight], but we didn't come through, so it was tough."
The Sox looked primed for a high-scoring game early on, as they created trouble for Rays starter Matt Garza. Ramirez's leadoff single in the second inning was followed by three straight walks. Garza, who was activated from the disabled list on Thursday night, threw 40 pitches in the inning, as the Sox batted around and put three runs across the plate.
But Boston was held to one run for the rest of the game, during which several of the sluggers struggled. Youkilis was 0-for-4 and Ortiz was 0-for-6, squandering several key at-bats.
"I'm not frustrated, [I'll] just keep playing," Ortiz said.
Francona said that Ortiz's last at-bat -- when the slugger hit a ground ball -- was a good swing, and that he wasn't angry with any player's effort in the loss.
"Everybody gets frustrated. We all want to win so bad," Francona said. "But we got guys on, we had the guys we wanted up, we just couldn't push a run across."
The skipper also lauded the effort by the Boston bullpen, particularly Mike Timlin, who took the loss after Carl Crawford scored the winning run on a right-field single by Nathan Haynes in the bottom of the 11th inning.
While warming up earlier in the game, Timlin experienced some lower back pain. But after getting some work done, the veteran reliever didn't hesitate to go out to the mound with the game on the line.
"For me, that's clutch enough," Francona said. "That's why he's still pitching the way he pitches, he made himself available. It didn't work out the way he wanted it to, but that's probably why you hear us brag about these guys."
Starter Tim Wakefield, who entered Friday's game a career 9-1 at Tropicana Field, struggled with control, issuing
five walks and a wild pitch, and hitting one batter over six innings. Three of his walks came in the second inning, when he loaded the bases with one out, but he retired the next two batters to escape the jam scoreless.
But the Rays would go on to tag the veteran knuckleballer for four runs (three earned) on six hits in six innings.
"I don't know how sometimes people catch it," Francona said of the knuckleball. "It was all over the place."
Wakefield, a Florida native, acknowledged that for "a couple of innings, it was uncontrollable," and said that the outing was a constant struggle.
"It was a battle for me tonight to try to make it through six innings," Wakefield said. "[You want] to manage the game well enough to keep us in the game."
Although the game was tied when Wakefield exited, the Sox let too many chances slip away, scoring only one run in the their final six at-bats.
The loss marks the first time the Sox have dropped three straight games since being swept at Toronto from April 4-6.