On June 25, 1923, a very unique golf match was held at the Olympia Field Country Club in Chicago, Illinois. It was a round of airplane golf, which pitted a team of nine professional golfers against nine amateur golfers.

So, you are probably wondering how would aerial golf work? Well, not as well as the event planners had hoped. The basic idea was that there were two airplanes from which golf balls would be dropped down as near as possible to the putting greens on the course below. The professional golf balls had white ribbons attached to them and the amateur balls had red ribbons. Wherever these balls landed, the players on the ground would substitute undecorated balls and attempt to drop them into the hole with the fewest number of strokes.

Things got off to a rocky start when one of the two airplanes involved hit a sprinkler during a practice run. As a result, the other airplane had to drop golf balls for both teams.

At the end of the match, the amateurs won by sinking the golf balls in twenty-five strokes.  The professionals took twenty-six strokes to do the same, although it was pointed out that the white ribbons attached to their balls were wider than the red ribbons, causing their balls to travel a greater distance before striking the green.

J.S. Conroy piloted the airplane for the winning team in the airplane golf match held at the Olympia Field Country Club in Chicago, Illinois. Image appeared on page 13 of the June 30, 1923 issue of the Palladium-Item