In his career, Connolly worked in an AL-record eight World Series: 1903, 1908 (even-numbered games), 1910, 1911, 1913, 1916, 1920 and 1924. He was also the home plate umpire for Addie Joss' perfect game on October 2, 1908, one of four no-hitters in which he called balls and strikes.