The best postseason win for the Expos was, of course, the seventh game of the 1994 World Series, in which the greatest Expo team of all time, led by star outfielders Larry Walker and Moises Alou, plus a pitching staff including ace Ken Hill, emergent Hall of Famer Pedro Martinez, and stud closer John Wetteland, beat the Yankees in a 15-inning thriller. It was, in fact, the greatest game that was never played.
But since we're constrained by the need to describe actual events, we'll go with the best of a limited set of options - 1981 NLDS Game 1: Expos 3, Phillies 1. Montreal started the best pitcher in team history, Steve Rogers, whose nickname obviously would have been Captain America if he'd played for almost any other team. Despite Rogers' excellence, they were still at a disadvantage against Philly's Steve Carlton, a Hall of Famer whose third-place finish in the '81 Cy Young voting was sandwiched between a pair of wins.
Quick note before we get to the actual game: Why was there an NLDS in 1981, when baseball didn't move to a three-round playoff format until 1995? As it turns out, it's for the same reason that the 1994 World Series is simply a figment of Canada's imagination: a strike. Baseball lost roughly the middle third of the '81 season to a labor stoppage, and when play resumed, instead of simply picking up with the season where it was left, the league decided to go with a split schedule - the teams who were in first at the time of the strike were designated the "first half" champions, and the rest of the season would be considered the "second half," and the first half and second half winners in each division would play each other in a pre-LCS playoff round.
It was an idea that could very literally be described as "bush league," since it's a common practice in the minors. It also resulted in the two teams with the best records in the National League, the Cardinals in the East and the Reds in the West, being left out of the playoffs. But on the bright side, it did give the Expos, a young team that had been trying to break through for years, their first crack at the postseason.
Captain Canada got off to a rough start in the top of the first, allowing a single, a walk, and a triple - but they were perfectly sequenced, as Lonnie Smith's leadoff hit was erased on a double play before Gary Matthews tripled, and Mike Schmidt's walk just put runners on the corners before Rogers escaped with a strikeout. Warren Cromartie led off the bottom of the inning with a single; Jerry White hit into a force but stole second, and scored the game's first run on Gary Carter's two-out double.
The Phils promptly tied it when Keith Moreland led off the second with a homer, but the Expos pulled back ahead on doubles by Tim Wallach and Chris Speier in the bottom of the inning. Pete Rose doubled in the top of the third, and eventually reached third before being left on; in the home half of the inning, Montreal loaded the bases on a White single and a pair of walks, but Wallach popped up and Jerry Manuel struck out to leave them that way.
Philly threatened again in the fourth, starting with a one-out Moreland single. After a groundout and an intentional walk brought Carlton to the plate, the pitcher singled, but Moreland was caught in a rundown at third - which doesn't make sense on a force play, so I guess he tried to score? Anyway, whatever happened, it was the third out of the inning, and the Expos tacked on another run with a Speier walk and a Cromartie double for a 3-1 lead.
The teams mounted intermittent threats from there; Rose singled in the top of the fifth, and Andre Dawson led off the bottom of the inning with a triple, but neither man scored. Speier walked in the sixth and made it as far as third before being stranded. In the seventh, Ron Reed replaced Carlton and allowed a single to Dawson, who then took third on a steal-and-error, and was once again abandoned there by his teammates. Smith led off the eighth with a single, becoming the first Phillie to reach in several innings, but was promptly caught stealing; the Phils mounted a better threat in the ninth, as Moreland singled and pinch hitter George Vukovich singled him to second, but Jeff Reardon relieved and struck out Manny Trillo to end the game.
This game was the less-common-than-you'd-expect matchup of two excellent pitchers that actually lived up to its billing. With that said, it was a relatively straightforward contest; after the fourth inning, the Phillies didn't put the tying run on base until there were two outs in the ninth. Most of the scoring threats came from the Expos, who went 3 for 20 with runners in scoring position - but they never trailed in the game, which kept their numerous failures from being imbued with too much drama.
Unlike their modern cousins, the Expos actually won their first playoff series; they then dropped the NLCS to the Fernandomania Dodgers (in a series that offers the second-best choice here, Rogers's complete game victory in Game 3). Almost exactly like their modern cousins (at least to this point), the Expos never made it this far again.
Fortunately, there are many happier times ahead in this series of posts, and one of them is up next, when we'll check in with the only team that remains in Canada.