In the 1914 U.S. Open, O'Brien was tied for fourth place after the first day, just 4 strokes behind Walter Hagen.

[3] Two disappointing rounds on the final day left him tied for 13th place, 12 strokes behind Hagen.

[5] In August, he finished tied for 6th place behind Walter Hagen in the Western Open and then in September he qualified for the final stage of the inaugural PGA Championship, finishing 4th in the qualifying of the Middle West section at the Glen View Club, with 7 places available.

For a number of years he had been running an indoor golf facility in East Liberty (Pittsburgh).

NYF = tournament not yet founded NT = no tournament WD = withdrew CUT = missed the half-way cut R64, R32, R16, QF, SF = round in which player lost in PGA Championship match play "T" indicates a tie for a place