Mike Flanagan and Steve Carlton did it first in 1983, representing the Orioles and Phillies, respectively.
The Braves' Greg Maddux and the Indians' Orel Hershiser did it twice in '95, and a year later, David Cone of the Yankees and Tom Glavine of the Braves pulled it off.
Three years later, Roger Clemens and John Smoltz followed suit, again for the Yankees and Braves.
CC Sabathia and Cliff Lee will join the extremely exclusive club on Wednesday at 7:57 p.m. ET at Yankee Stadium -- and form a new club at the same time.
Cy Young Award pedigrees in hand, Sabathia and Lee will square off in Game 1 of the World Series, marking the sixth time in history that former Cy Young winners have squared off.
"I think that's a pretty good matchup," understated typically understated Phillies manager Charlie Manuel.
There's no understating the rarity of such a matchup, though. Aside from the aforementioned examples and what will go down in Game 1, only a handful of World Series games have even come close to featuring a pair of previous Cy Young winners.
For instance, Dwight Gooden had won the National League Cy Young for the Mets the previous year when he took on Clemens -- then with the Red Sox -- in Game 2 of the 1986 World Series, but Clemens was still a few weeks away from claiming his first Cy Young.
And were the Cy Young Awards doled out before the Fall Classic instead of after it, 1968 would have been the ultimate example.
There were no better pitchers in the game that year than Denny McLain of the Tigers and Bob Gibson of the Cardinals, who locked horns in Games 1 and 4. They were officially named the NL and American League Cy Young Award winners in the aftermath.
Game 1 on Wednesday will be just the sixth time two former Cy Young Award winners will face off in a World Series game -- and the first time two former Cy-winning teammates will do so.
October 14, 1983
Game 3 at Veterans Stadium Orioles LHP Mike Flanagan vs. Phillies LHP Steve Carlton Orioles won game, 3-2 (won Series, 4-1) Flanagan (ND) 4 IP, 6 H, 2 R, 2 ER, 1 BB, 1 K Carlton (L) 6 2/3 IP, 5 H, 3 R, 2 ER, 3 BB, 7 K
October 21, 1995
Game 1 at Atlanta-Fulton County Stadium Indians RHP Orel Hershiser vs. Braves RHP Greg Maddux Braves won game, 3-2 (won Series, 4-2) Maddux (W) 9 IP, 2 H, 2 R, 0 ER, 0 BB, 4 K Hershiser (L) 6 IP, 3 H, 3 R, 3 ER, 3 BB, 7 K
October 26, 1995
Game 5 at Jacobs Field Indians RHP Orel Hershiser vs. Braves RHP Greg Maddux Indians won game, 5-4 Hershiser (W) 8 IP, 5 H, 2 R, 1 ER, 1 BB, 6K Maddux (L) 7 IP, 7 H, 4 R, 4 ER, 3 BB, 4 K
October 22, 1996
Game 3 at Atlanta-Fulton County Stadium Yankees RHP David Cone vs. Braves LHP Tom Glavine Yankees won the game, 5-2 (won Series, 4-2) Cone (W) 6 IP, 4 H, 1 R, 1 ER, 4 BB, 3 K Glavine (L) 7 IP, 4 H, 2 R, 1 E, 3 BB, 8 K
October 27, 1999
Game 4 at Yankee Stadium Yankees RHP Roger Clemens vs. Braves RHP John Smoltz Yankees won game 4-1 (won Series, 4-0) Clemens (W) 7 2/3 IP, 4 H, 1 R, 1 ER, 2 BB, 4 K Smoltz (L) 7 IP, 6 H, 3 R, 3 ER, 3 BB, 11 K
The Gibson-McClain clashes in the "Year of the Pitcher" were the first of two successive such matchups. In 1969, the Mets' Tom Seaver and the Orioles' Mike Cuellar faced off in the Fall Classic and later earned the hardware for their respective leagues.
And the Gooden-Clemens pairing in '86 was the latest of three instances of a former Cy Young Award winner dueling a hurler who would be so honored following that year's World Series. It happened twice in the era before 1967 when one Cy Young Award was doled out for both leagues. In 1963, Whitey Ford (who won in '61) faced '63 winner Sandy Koufax in Games 1 and 4 of the Dodgers' sweep over the Yankees. In 1960, the Yankees' Bob Turley (who won in '58) started Game 7 against '60 winner Vern Law of the Pirates, but neither pitcher received a decision when Bill Mazeroski ended the Series with his famous home run.
This kind of thing simply doesn't happen much. Walk-off homers are more common in the World Series, and that's pretty much all you need to know.
This particular matchup, though, has an extra dose of intrigue to it.
Sabathia, of course, will be donning the iconic pinstripes of the Yankees, who are looking for their 27th world championship. Lee is the ace of the Phillies, who are looking to become the game's first back-to-back champs since the Bronx Bombers won three in a row from 1998-2000.
And like those 1968 battles between McLain and Gibson, this year's matchup pits two pitchers at the absolute top of their games.
Sabathia, a top candidate for this year's AL Cy Young after a stellar first season in New York, was named the AL Championship Series MVP on Sunday and is 3-0 with a 1.19 ERA in three postseason starts this year.
Lee, last year's AL Cy Young Award winner, is 2-0 with an 0.74 ERA in three starts this October.
"CC loves to pitch and he's very competitive, and Lee has the same kind of makeup, too," Manuel said. "So it has a chance of being a good game."
It has a chance of being three good games, actually. Neither manager is tipping his hand, but if the Series goes the distance, it's feasible that Sabathia and Lee could square off in Games 4 and 7, too.
Should that happen, it'll bring into even sharper focus the relationship between the two mound masters, and that relationship is what makes this matchup particularly tasty.
Sabathia and Lee were teammates with the Indians from 2002-08.
"We have two Cleveland Cy Young Award winners going against each other," mused Manuel, who managed the Indians from 2000 to mid-2002
Less than a year after picking up his first Cy, Sabathia was traded by the Tribe to the Brewers last summer and parlayed his success with Milwaukee into free-agent riches with the Yankees.
Lee was traded to the Phillies this summer, prompting a fan to unfurl a banner during the NLCS thanking the Indians for the help.
The man who engineered both trades, Cleveland general manager Mark Shapiro, has mixed feeling about seeing his former formidable one-two punch shining so bright this fall.
"It's bittersweet," Shapiro said Monday. "You don't work in this game without building a personal attachment to guys. So I look out there and see those two guys, and, as people, I'm excited for them. I'm excited for them to show their talent on that stage, I'm excited for them to get that type of exposure.
"And yet I'm bitter that they're not doing it in the Indians uniform."
Sabathia said he still texts with Lee frequently, and he beamed at the possibility of getting to hit off Lee when the series moves to Philadelphia.
The two faced each other on April 16, in the first regular-season game at New York's $1.5 billion behemoth of a baseball cathedral. Lee got the win, Sabathia a no-decision.
"That was a pretty big game, too," Sabathia said.
Mychael Urban is a national reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.