Osmond trained in southern California for about two weeks in August 2013 under the guidance of Walia and Frank Carroll. Due to a stress reaction in her left ankle, she was off the ice for most of September 2013. In late October, she competed at the 2013 Skate Canada International, placing fifth in the short program, but pulled out before the free skate due to a torn hamstring in her right leg. She also withdrew from the 2013 Rostelecom Cup but returned to competition at the 2014 Skate Canada Challenge. At the 2014 Canadian Championships, she placed first in both segments and repeated as national champion.