Before Ryan Dempster signed with the Red Sox in the offseason, he rarely pitched against the Yankees, spending the vast majority of his career in the National League as a member of the Marlins, Reds, and Cubs.
He pitched against them in 1998, 2000, and 2001, and didn't face them again until 2011. He faced them once in 2012 as a Texas Ranger, and once earlier this season.
Each time, victory eluded the veteran, leaving him 0-5 with a 6.98 ERA in seven career starts as he entered Sunday night's game opposite Yankees lefthander CC Sabathia.
After 5⅓ innings and with a 6-4 lead, Dempster exited to a standing ovation from the sold-out Fenway crowd of 37,917 — presumably for plunking Alex Rodriguez in the second inning.
But the righthander left the Red Sox in a precarious position, the Yankees with the bases loaded, jeopardizing his chance for an elusive victory.
"I'm more disappointed in the fact I couldn't hold a 6-3 lead," said Dempster, who threw 107 pitches. "That's the bigger story. I didn't do a very good job of making pitches in the sixth inning. I have to execute better. Guys go out there and score a bunch of runs off a guy like Sabathia and you have to make your pitches, and I didn't do that."
Rodriguez led off the sixth inning with a home run to the center-field bleachers, turning on an 89-mile-per-hour fastball. As he rounded first, Rodriguez pumped his fist, his satisfaction visible after being hit by Dempster earlier.
Dempster then surrendered a pair of one-out singles to Eduardo Nunez and Lyle Overbay, and walked Chris Stewart.
"We saw later on when he doesn't establish his fastball in," said Red Sox manager John Farrell. "Whether it was Stuart, Nunez, Rodriguez, you look back at all three, the approach, the plan was to establish hard in.
"Up three starting the sixth, ideally you're thinking where he was getting at his pitch count and at the bottom half of the order, I felt like he could get through that relatively easy. All of a sudden, he seemed to hit a wall. He lost his command, particularly the four-pitch walk to Stewart."
The walk capped Dempster's night, as Drake Britton entered to try to squelch the Yankees' rally. But Brett Gardner sent the second pitch from the lefthander, a slider that hung in the zone, into the right-center gap for a three-run triple that gave the Yankees a 7-6 lead, and led to a 9-6 win.
"It was a tough spot, I wanted to get out of that inning so bad for Demp," Britton said. "I wanted to go slider out of the zone and I left it up in the zone and he hit it."
Just as Britton expressed his disappointment over not getting out of the jam, Dempster uttered his own frustration about letting the game slip away.
"When you sit there and let them creep back in it, especially the bottom of the lineup, that's a time you have to close the door," Dempster said. "Then, to hand the ball over to somebody to expect them to get out of bases loaded, that's a lot to ask. I just didn't do my job tonight. That's the part I'm most angry with."
With a six-game West Coast trip starting Monday in San Francisco, Dempster's early exit had an greater impact on the Sox' bullpen, as Farrell used five relievers.
"Their bullpen held us down, ours didn't," Farrell said. "We didn't follow up one after the other with quality outings."
After Gardner's triple, Britton got Ichiro Suzuki to ground to shortstop Stephen Drew, who fired home to get Gardner. After a single by Robinson Cano, Brandon Workman relieved Britton and finished the sixth.
Morales, Junichi Tazawa, and Rubby De La Rosa also came on in relief for the Red Sox.
"It was unfortunate, obviously we wanted it to go a little bit different," Britton said. "I certainly did. But tomorrow's a new day. I'm not going to dwell on this. We were ahead until I came in the game. Did the best I could, but we got a big series coming up on the West Coast and I'm just going to focus on that."