This is oldest known derby patch of which I'm aware.  Its history goes back to August 13, 1935 when Leo Seltzer held a month-long event in Chicago he called Transcontinental Roller Derby.  It was the simulation of a 3000-mile cross-country roller skating race in which 25 two-person (male-female) teams circled an oval banked track made of wood.  They would skate for 11.5 hours a day, and a team was disqualified if both members were off the track during skating times.  Only 9 of 25 teams finished the race.  He later took the sport to other venues around the United States.  Certain periods of time allowed physical contact between the skaters, a development that was highly popular with the audience.  He later reformed the event to minimize time and maximize contact, and a new sport was born.  This patch is likely from sometime in the mid-late 1930s.