Each has won 10 of those games and lost 10 of those games. The run differential over those 20 meetings is a scant two runs: 99 for the Yankees, 97 for the Orioles.
And after Monday night’s 3-2 Orioles victory at Camden Yards, the American League Division Series is knotted at one game apiece.
If ever two teams seem practically attached at the hips, it is the Yankees and Orioles. Remember, they spent the month of September virtually tethered to one another until the last two games of the regular season, when the Yankees were finally able to wedge two games between them.
But now, those two games have vanished into the cold October night.
The Yankees and Orioles are tied once again, but as difficult as it is to believe considering what has gone on between them over the past six months, by the end of business Friday we will have a definitive winner to this fight, even if the margin of victory turns out to be a single game.
But the truth is, it needn’t have been this tough for the Yankees.
In Game 2, they had Andy Pettitte, who may not be their ace but is certainly their ace in the hole when it comes to postseason experience and performance.
Pettitte worked all the way into the eighth inning, held the Orioles to seven hits and three runs and was really only in trouble in one inning. He gave the Yankees not only a game they should win in the regular season, but a game they must win in the postseason.
They didn’t win it, and now, Pettitte is gone for the rest of the ALDS, that round having been fired out of their chamber.
And suddenly, the Yankees face another three-game series against the Orioles, and they must take two of three or their season is over.
The reason they find themselves in this spot is not because of Pettitte and how he let his command get away from him long enough in the third inning for the Orioles to score two runs, or about the slider that Mark Reynolds hit just beyond Robinson Cano’s reach in the sixth inning to drive in the decisive third run.
The Yankees are where they are now, one loss away from a huge decision for Joe Girardi and two losses away from a second-straight first-round KO, for the same reason they struggled so mightily through the second half of July, all of August and much of September, and for the same reason they never could shake the stubborn Birds out of their tree.
They are here at the precipice for want of a timely hit.
The game was not lost in the third or the sixth inning by Pettitte, nor was it lost when Baltimore second baseman Robert Andino speared Alex Rodriguez’s liner with runners on first and second and none out in the first to start a damaging double play.
It was lost where a lot of Yankees games were lost this season. In the clutch.
And when they got a leadoff double from Nunez, an RBI single from Jeter, a stolen base, a walk and a wild pitch that advanced two runners to second and third -- only to have Nick Swisher fly out to medium left field to kill that threat.
By the time A-Rod swung over a Jim Johnson fastball to end the game, he may have been an easy target, but the shooters were off the mark.
The game the Yankees lost Monday night is a game they have lost many times before this season, but a game they will not get too many chances to lose again.
“I believe these guys are going to come through," Girardi said, in what is beginning to sound like a phonograph record with a skip in it. “I believe they’re going to put good at-bats together, they’re going to keep putting runners on, and they’re going to break through. I believe in them."
Blind faith is a wonderful thing, if a bit irrational, and a wiser man than me once said that the definition of crazy is doing the same thing over and over again but somehow expecting different results.
By that definition, Girardi and the Yankees are crazy.
They may well put together good at-bats, and put runners on, and eventually break through. But if they can’t find a way to do it twice in the next three games, it will have to wait until next season.
“That game was very frustrating for us," said Rodriguez, who had single in the third inning, putting runners on first and second, a threat that went nowhere when Cano grounded out. “We had a lot of opportunities starting in the first. We wasted a great performance by Andy.”
Russell Martin, Sunday’s hero, played Monday’s contrarian.
“Wasted opportunity? I don’t know," he said. “It’s part of the game. You’re trying to make something happen and sometimes you don’t. Sometimes you hit the ball hard and it gets caught. It’s not something to go crazy about. I feel like we’re a good team and we’re going to give them a hard time at home."
Speaking of which, the Yankees have not given the Orioles much of a hard time at Yankee Stadium, where the series relocates for its final three games. The Yankees dropped six of nine games at home to Baltimore during the regular season, being outscored 49-32.
“We wanted to win today," Jeter said. “We like playing at home and I'm sure the fans will be ready. The bottom line is we have another game in New York and one we need to win."
The burden will ostensibly be on Hiroki Kuroda, though in fact, it will be on this all-or-nothing offense, which is certainly more dangerous in its homer-friendly ballpark, where the Yankees hit 138 of their 245 home runs this season.
But as they have all season, the Yankees demonstrated Monday night that they are a far less dangerous offensive team when they do not hit the ball out of the park -- they were 88-43 this season when hitting at least one home run, 7-24 when they were kept in the yard.
And once again, in Monday night’s loss, they were 2-for-8 with runners in scoring position, and one of those two hits did not even drive in a run.
If it seems like an old and tired story, it’s only because it has been told so many times this year.
And if we’re telling it again after Wednesday night’s Game 3, the story of this season might be heading into its final chapter.
Predictably enough, Pettitte blamed himself for the defeat.
“I felt really good early, and pretty suspect after that," he said. “After the first two innings, I felt like my stuff wasn’t very crisp. I made a mistake to Davis, left him a ball right in the middle of the zone, and that pretty much cost us the game."
In fact, it cost the Yankees two runs, and that should not have been enough to cost them a playoff game.
But for the want of a timely hit, it did, and now, after 20 toe-to-toe meetings, the Yankees and Orioles find themselves right back where they started six months ago.
Dead even, with three games for one team or the other to prove which is boss.
“It’s been this way all season; we win one, they win one," Swisher said. “It’s been a battle. These have been fun games."
The Yankees now have three games to figure out a way to win this battle, or by Friday night, the fun stops until next year.