After solid seasons in 1906 (15–10, 2.53), 1907 (16–8, 2.05), 1908 (8–9 despite a 1.75 ERA, and 1909 (18–8, 1.66), he led the Athletics to the AL pennant in 1910, as Philadelphia went 102–48, games ahead of the second-place New York Yankees. Bender led the AL in winning percentage, at .821, going 23–5 with a 1.58 ERA. He went 1–1 with a 1.93 ERA in the World Series as the A's beat the Chicago Cubs, who had gone 104–50 in the regular season, in five games. Bender pitched a complete-game three-hitter in the opener, striking out 8 and giving up only one unearned run. He lost Game 4 of the series in another complete-game effort, 4–3 in 10 innings. Bender pitched all innings for the Athletics, striking out 6.