Endicott was working as a farmer until his racing career began in 1902. He started 14 events in late 1909 to early 1910; he won ten of them and finished second in the other four. He won nine more races by the end of 1910. Endicott set a 24 hour endurance record at Brighton Beach Dirt Track by completing in 18 hours. He also set record times for 5, 10, 25, 75, and 100 miles at Beverly Hills Speedway. Endicott raced throughout the United States at dirt tracks with wins at Atlanta (GA), Louisville (KY), and Long Island (NY). In 1912, he finished fifth in the Indianapolis 500. Endicott also had dirt wins at Old Orchard (ME), Fond du Lac (WI), Milwaukee Mile, and Peoria (IL). He retired from racing after his brother Harry died in September 1913.