Eddie Shore continued to hold out and sat in Section 33 for the Boston Bruins home opener on November 15, 1938 against the Maple Leafs. Constant chants from fans for his return soured the mood and the game ended in a 1-1 tie. Jack Crawford set up Cooney Weiland for Boston's goal and Conn Smythe sang Crawford's praises. He told the press that he'd purchase him for $10,000 and also offered the same sum for each member of the Kraut Line. With two extra forwards comprising the "fourth line", Art Ross kept mixing the lines up.
Before the Bruins game against the Maple Leafs on February 7, Art Ross attended a fete of the Gridiron Club. A long standing rivalry with Conn Smythe was addressed as the two sat together and buried the hatchet. Each aired their grievances ending with Smythe praising Ross' accomplishments and relating that the two of them were "working towards the same end, that of putting the NHL on the highest plane possible." They vowed the feud was over except when their clubs played each other. With Ray Getliffe dispatched to the minors, the game featured a new third line of Terry Reardon, Red Hamill and Gord Pettinger. Several Bruins also wore Ross' latest invention, "gators" to protect the back of their legs from cuts.
The Leafs opponent was the Boston Bruins, who finished the season with a 36–10–2 record, earning 74 points, which was 27 points more than the Leafs. The Bruins defeated the New York Rangers 4 games to 3 in the Semi-Finals and went into the series the favorites, sporting new uniforms with gold added to the shoulders, pants and socks.
Game 1 in Boston was a tight-checking affair with Woody Dumart opening the scoring at the 16:04 mark of the first period with the first playoff goal of his career. The Leafs tied it up in the third with the first of the playoffs for Red Horner but less than three minutes later, Bobby Bauer won it for the Bruins.
Game 3 in Toronto was scoreless in the second period when Eddie Shore checked Leafs star Busher Jackson, dislocating his shoulder. Jackson missed the remainder of the series. Disheartened, the Leafs gave up goals by Bauer, Conacher and defenseman Jack Crawford (first playoff goal of his career). A last minute goal by the Leafs Gus Marker wasn't enough as the Bruins won 3-1.
Game 4 in Toronto saw the Bruins go ahead 1-0 early in the game on a power play goal by Conacher, assisted by Hill. The Bruins Frank Brimsek shut the door and earned his first playoff shutout as the Bruins won 2-0 after Conacher added his second of the game, assisted by Hill and Bill Cowley.
Game 5 in Boston saw Hill score his 6th of the playoffs at 11:40 of the first period while Gord Drillon was in the penalty box. Toronto countered with a power play marker of their own when Kampman scored at 18:40 on a point shot, that deflected off Dit Clapper's skate, with Hill in the box. With the score tied 1-1 late in the second period, Conacher broke in on a breakaway and fired the puck over Broda's left shoulder, his 6th goal of the playoffs. This put the Bruins up 2-1, which would prove to be the winner. The Leafs frantically tried to tie it up in the third and had a perfect opportunity when Eddie Shore took a penalty with 2 minutes to go. However, the Leafs Nick Metz, who'd been called up as Busher Jackson's replacement, took a penalty and the teams skated four on four. With 37 seconds left, Flash Hollett widened Boston's lead to 3-1. The Bruins took the series and the Cup 4 games to 1. Frank Brimsek held Toronto to just six goals in five games. Bill Cowley led the playoffs in scoring with 11 assists and 14 points.