Game 1

Game 1 of the Series matched the Yankees' Red Ruffing, who had won 21 games during the season, against the Cubs' 22-game winner Bill Lee. In the top of the second inning, Lou Gehrig walked and moved to third on a single by Bill Dickey. George Selkirk then reached on an error by Cub second baseman Billy Herman scoring Gehrig, and Joe Gordon drove Dickey in with a single for a 2–0 Bomber lead.

In the bottom of the third, the Cubs cut the lead in half when Ripper Collins singled to lead off and moved to second on a groundout by Lee. Stan Hack's single to right scored Collins, Hack taking second on the throw home. But when he attempted to score on an infield single by Herman, he was gunned down at home. The top of the sixth saw New York extend its lead to 3–1 when Tommy Henrich belted a double to right and scored on a Dickey single. The Cubs could muster nothing further off Ruffing, who scattered nine hits over the course of the game, and the Yankees held on for the win and a 1–0 lead in the Series.

Game 2

Game 2 pitted the Yankees' Lefty Gomez against former St. Louis Cardinals ace Dizzy Dean, who had been traded to Chicago in April and won seven of his eight regular-season wins for his new team on finesse after having lost his fastball by changing his pitching motion to avoid putting weight on the toe he had fractured during the 1937 All-Star Game (on a low line drive back to the mound by Earl Averill). Game 2 of the 1938 Series thus became known as "Ol' Diz's Last Stand".

The Cubs gave Dean a 1–0 lead in the bottom of the first inning when Hack singled, advanced to third on a single by Frank Demaree and scored on Joe Marty's fly ball. But the Bronx Bombers took the lead in the next half-inning when a Gordon double scored both Joe DiMaggio and Gehrig. In the bottom of the third, the Cubs went back out in front by a run when Hack and Herman hit back-to-back singles, were sacrificed to third and second by Demaree, and scored on Marty's double.

Dean pitched effectively for the next four innings, giving up only a single to Gehrig in the fourth. But in the top of the eighth, the Yankees stormed back on a two-run homer by Frankie Crosetti that scored pinch-hitter Myril Hoag for a 4–3 Bomber lead, and DiMaggio added a two-run dinger of his own in the top of the ninth that scored Henrich. Johnny Murphy, in relief of Gomez, held Chicago at bay for the final two innings for a 6–3 Yankee win as the Series moved east to New York with a 2–0 Series advantage for the Yankees.

Game 3

For Game 3 at Yankee Stadium, the Cubs threw Clay Bryant against the Bombers' Monte Pearson. Both pitchers matched zeroes for the first four innings. In the top of the fifth, the Cubs drew first blood when Hack doubled, moved to third on Gordon's error on Phil Cavarretta and scored on Marty's forceout of Cavarretta at second. In the bottom half of the inning, however, Gordon atoned for his mistake by walloping a solo home run off Bryant to tie the game. Pearson followed with a single to right, advanced to second on a Crosetti walk and scored on a Red Rolfe single to give the Yankees a 2–1 lead.

In the bottom of the sixth, New York tacked on two more runs with a two-run single by Gordon. In the top of the eighth, the Cubs cut the lead in half when Marty hit a home run to notch his fifth RBI of the Series, but Dickey answered for the Yankees with a shot of his own in the bottom half. The Bombers held on for a 5–2 win and a 3–0 Series stranglehold.

Game 4

Game 4 was a rematch of the Game 1 starters, Ruffing vs. Lee. Like the closely contested series opener, it stayed close until New York pulled away with four runs in the bottom of the eighth.

In the bottom of the second, the Yankees struck for three runs. Hoag reached on Hack's throwing error from the hot corner, and advanced to third on a Gordon single. Ruffing helped his own cause by singling in Hoag, and Crosetti's triple to left scored Gordon and Ruffing. The Cubs broke the shutout with a Billy Jurges fielder's choice scoring Demaree, but in the sixth the Bombers got the run back with Henrich's solo homer off veteran Cub reliever Charlie Root.

In the top of the eighth, the Cubs cut the New York lead to one with a Ken O'Dea home run scoring Cavarretta ahead of him. But in the bottom half, the Yankees broke the game open with a four-run outburst off four Cub pitchers—Vance Page, Larry French, Tex Carleton and Dean. Crosetti drove in two with a double off Dean, giving him four RBI for the game and six for the Series. As in Game 1, Ruffing went the distance, allowing two earned runs and eight hits with six strikeouts.

This was the last World Series game ever played by Yankee first baseman Lou Gehrig. He had one hit in four at-bats. Defensively he had five putouts and two assists.