[1][2] Roy Waldron had a short career as a jockey but his ongoing employment in horse racing was interrupted by service in World War I with the United States Army, Fifth Company, 157th Depot Brigade.
When the War ended, Roy Waldron returned to racing as part of the training operations with Xalapa Farm in Paris, Kentucky under manager James McClelland.
By the early 1920s he would be training a string of horses for the Lexington Stable, the nom de course for Xalapa owner Edward F. Simms and racing partner Henry W.
[3] Waldron's most important win for the Lexington Stable came in the 1924 Jockey Club Gold Cup with My Play, a full brother to the great Man o' War.
[7] After Hope Iselin decided to get out of racing, in August 1938 Roy Waldron accepted an offer to take over as trainer of the Milky Way Farm Stable of Ethel Mars.
[12] Oddsmakers considered Mioland the only horse with even an outside chance of beating the undefeated Bimelech and sent the Charles Howard colt off as a 6:1 second choice with Gallahadion relegated to a 35:1 longshot.
Heavy favorite Bimelech, who had led the race by a head after a mile and increased it to a half-length coming down the stretch, could not hold off the charge of Gallahadion who won by a length and a half.