But these are different times, and Damon stung his former team on Tuesday night by belting a two-run homer off Daisuke Matsuzaka that helped lift the Yankees to a 5-3 victory over the Red Sox.
Damon's blast came in the bottom of the seventh, just moments after Jason Varitek tied the game for Boston in the top of the inning by placing one just over the outstretched glove of Damon and into the left-field stands.
"He tried to come in on Johnny," Red Sox manager Terry Francona said of Matsuzaka. "Even though the ball didn't catch the great part of his bat, because it wasn't in enough, he was able to not only keep it fair, but in a perfect part of the ballpark. [Matsuzaka] didn't locate it, and he got enough of it to get it out of the ballpark."
The Red Sox then got their initiation to young Yankees setup man Joba Chamberlain, who registers triple digits on the radar gun at times. The fireballer worked around a hit and a walk and struck out two, setting up last call for Mariano Rivera.
The venerable closer put the Red Sox away with a 1-2-3 ninth, punching out two.
"Really no different," Varitek said of Rivera. "Still the same guy. Cutters both sides, occasional sinker. He's the same guy."
Aside from losing the game, the Red Sox also lost Manny Ramirez in the seventh inning to back spasms. There's a chance Ramirez will be out of the lineup on Wednesday night when Boston faces Roger Clemens for the first time since 2003.
The 80-52 Sox still lead the Yankees by seven games in the American League East.
Matsuzaka, who is winless in his last four starts, slipped to 13-11. Over 6 1/3 innings, Matsuzaka allowed six hits and five runs, walking three and striking out two.
"Yes, I did sort of abandon the strikeout and try to keep my pitch count low and go deep into the game," Matsuzaka said through translator Masa Hoshino.
Though Matsuzaka is 2-1 vs. the Yankees, he hasn't had a quality start in any of his three outings against New York.
"I think that each hitter in their lineup is very highly skilled," said Matsuzaka. "I knew that leaving any pitch in a soft location against any batter in their lineup could result in a long extra-base hit. Personally, the home run was obviously something that I wanted to avoid the most."
As usual, Matsuzaka didn't seek excuses.
"I think that all the responsibility for our recent losses belongs to me," said Matsuzaka, who in fact has taken the ball in both of Boston's last two defeats.
The right-hander had a shaky first inning, hitting Alex Rodriguez on the back to load the bases with one out. Hideki Matsui brought home the first run of the game with a fielder's-choice grounder to second. Jorge Posada slammed a double down the line in left to make it 2-0. Matsuzaka threw 26 pitches in the inning.
"You know, the first inning, I thought he tried to limit the damage," said Francona. "I actually thought he made a pretty good pitch on [Bobby] Abreu that wasn't called. He gave up two quick ones. But we come back, and then I thought he settled in pretty well."
Ramirez got one of the runs right back for Matsuzaka by lofting an opposite-field homer to right off Andy Pettitte. It was career homer No. 490 for Ramirez and his 52nd against the Yankees. Ramirez ended up leaving the game in the bottom of the seventh with muscle spasms in his lower back.
Back came the Red Sox in the third. Julio Lugo led off with a triple and scored on a sacrifice fly to left by David Ortiz.
For a while, Matsuzaka settled down. But Derek Jeter took his front-door cutter over the wall in right to put the Yankees back on top in the bottom of the fifth.
It was fair to wonder which mistake pained Matsuzaka more -- the home run ball to Jeter or Damon.
"I think both were definitely pitches that could have been prevented, so I definitely regret both," Matsuzaka said.
If the Red Sox's rotation stays on track, Matsuzaka will get another crack at the Yankees on Sept. 14 at Fenway Park.
Ian Browne is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.