Pitkeev started the 2015–16 season on the Challenger Series, placing fourth at the 2015 Ondrej Nepela Trophy. A recipient of two Grand Prix invitations, he placed 5th at the 2015 Skate America before winning his first GP medal, silver, at the 2015 Rostelecom Cup. In December, he was awarded the bronze medal at a CS event, the 2015 Golden Spin of Zagreb, behind Adam Rippon of the United States. Later that month, he placed 3rd in the short, 11th in the free, and 9th overall at the 2016 Russian Championships. He competed with a back injury at the Russian nationals and had to take painkillers. He later underwent treatment in Germany, the United States, and Russia.