O'Loughlin is well remembered for a call during the 1907 pennant race that went against Connie Mack's Athletics in a game against Detroit. The call concerned possible interference by a policeman with a Detroit defender. It appears that O'Loughlin did not initially note any interference, but after conferring with fellow umpire Tommy Connolly, the Athletics batter was called out. Mack angrily protested, later going so far as to send affidavits from nearby fans and the policeman to league president Ban Johnson. The game was ultimately called a tie on account of darkness after seventeen innings and the second game of the scheduled doubleheader was postponed. Though Mack's team would finish 1 1/2 games out of first place, Mack would still blame O'Loughlin for the loss of the pennant more than forty years later.