A fine outfielder with a light bat, Sullivan went 0-for-11 in his rookie season for the Senators. He received a great deal of playing time with Boston before Tris Speaker replaced him at center field. His most productive season came in 1907, when he posted career-highs in games (144), batting average (.245), hits (135), runs (73), RBI (26) and on-base percentage (.315). Traded to Cleveland in the 1908 midseason, he also played seven games for the Naps in parts of two seasons.
In a four-year career, Sullivan was a .239 hitter (221-for-925) with one home run and 51 RBI in 255 games, including 106 runs, 25 doubles, eight triples, and 30 stolen bases.