Dolensky composed his own music, "Windfall", for his 2011−12 short program. He competed at two JGP events, winning bronze in Riga, Latvia and placing 4th in Innsbruck, Austria. He was awarded the silver medal in the junior event at the 2012 U.S. Championships and was sent to the 2012 World Junior Championships. Dolensky finished 12th overall at the event in Minsk, Belarus, having ranked 9th in the short program and 13th in the free skate.