1969 Montreal Expos season

Offseason

The Montreal Expos took part in the 1968 Major League Baseball expansion draft on October 14, 1968. On October 16, Don Bosch was purchased from the New York Mets, and on October 21, Bob Bailey was purchased from the Los Angeles Dodgers.

Floyd Wicker was drafted from the St. Louis Cardinals in the 1968 rule 5 draft on December 2. On January 22, 1969, Donn Clendenon and Jesús Alou were traded to the Houston Astros for Rusty Staub; Clendenon refused to report, and the Expos later sent Jack Billingham, Skip Guinn, and $100,000 to the Astros on April 8 as compensation. The Expos and three other expansion teams were allowed to participate in the June 1968 MLB first-year player draft but were barred from the first three rounds; they drafted 15 players, none of whom reached the majors, and all but five went unsigned.

Regular season

The Expos played the first international game in MLB history on April 8 at Shea Stadium in New York City. Bob Bailey recorded the first hit and extra-base hit in franchise history with a double in the first inning, and relief pitcher Dan McGinn hit the first home run, a two-run shot off Tom Seaver in the fourth. On April 14, Mack Jones hit a three-run home run and a two-run triple in an 8–7 win over the St. Louis Cardinals, the Expos' first home victory at Jarry Park; Jones' blast was the first MLB home run hit outside the United States, and McGinn became the first MLB pitcher to win a game outside the United States. On April 17, in just the franchise's ninth game, Bill Stoneman pitched a 7–0 no-hitter against the Philadelphia Phillies at Connie Mack Stadium, striking out eight; Rusty Staub went 4 for 5 with three doubles and a homer.

Roy Face was signed as a free agent on April 27. On June 3, Mudcat Grant was traded to the St. Louis Cardinals for Gary Waslewski. On June 11, Maury Wills and Manny Mota were traded to the Los Angeles Dodgers for Ron Fairly and Paul Popovich, and later that day Popovich was traded to the Chicago Cubs for Adolfo Phillips and Jack Lamabe. On June 15, Donn Clendenon was traded to the New York Mets for Kevin Collins, Steve Renko, Bill Carden (minors), and Dave Colon (minors).

Roy Face was released on August 15. Claude Raymond was purchased from the Atlanta Braves on August 19. Marv Staehle was purchased from the Seattle Pilots on September 13. Terry Humphrey was drafted in the 39th round of the 1969 MLB draft on June 5.