The Giants finally got to Yankee starter Bullet Joe Bush in the eighth, rallying for three runs and riding Ryan in the ninth for the 3–2 win. The Giants went on to sweep the Bronx club for their second consecutive title. In the 1923 World Series, Giants' Game 1 starter Mule Watson allowed three Yankee runs in the first two innings, and was lifted for Ryan, who twirled the final seven innings, allowing only one additional Yankee run in the Giants' 5–4 win. Ryan was used briefly in the Giants' Game 4 loss, and then came on in relief of starter Art Nehf in Game 6. With the Yankees leading the best-of-seven series three games to two, Nehf and the Giants led the do-or-die sixth game after seven innings, 4–1. Nehf loaded the bases in the eighth and then walked in the Yankees' second run of the game. Ryan was brought in with the bases loaded and one out. He proceeded to walk Joe Dugan to force across a third Yankee run, but then with the bases still loaded, he fanned the mighty Ruth. With two down, Yankee batter Bob Meusel singled to drive in all three runners, and the Yankees took a 6–4 lead. The Giants failed to score in the bottom of the eighth, and Ryan set down the Yanks in order in the ninth, but the Giants could not rally in the final frame. Ryan took the loss, and the Yankees had their first World Series championship. Ryan went 7–6 in 37 appearances for the 1924 Giants, and made two appearances in the Giants' seven-game World Series loss to the Washington Senators. He tossed 4.2 innings of middle relief and allowed two earned runs in New York's 6–4 Game 3 win, but his moment of glory came at the plate, as he belted a fourth-inning homer to deep right field off Senators' hurler Allen Russell. Ryan was only the second pitcher ever, and the first relief pitcher, to hit a home run in World Series play. Ryan was traded to the Boston Braves for Tim McNamara prior to the 1925 season, and posted a lackluster 2–8 record with a 6.31 ERA in 37 appearances for Boston. He fared no better in 1926, beginning the season with a 7.58 ERA in seven appearances for Boston, before being shipped off to the minor league Toledo Mud Hens, where he toiled into the 1928 season. He joined the New York Yankees late in their 1928 season, appearing in three games and allowing 11 earned runs in six total innings.