[7] Kayne/O'Shea returned to competition at the 2014 Golden Spin of Zagreb, taking bronze at the ISU Challenger Series (CS) event.

[8] Making their Grand Prix debut, the pair placed sixth at the 2015 Skate America and fourth at the 2015 Rostelecom Cup.

[9] In January, Kayne/O'Shea placed first[10] in both segments at the 2016 U.S. Championships and won the gold medal by a margin of 14.85 points over defending champions Alexa Scimeca / Chris Knierim.

The pair withdrew from the 2017 U.S. Championships due to a concussion, Kayne having hit her head while attempting a throw triple flip during the short program on January 19.

[8] She received a new cadaver tendon in an operation at the Vail Valley Medical Center on February 14, 2017, and then refrained from walking for seven weeks.

[13] At the 2018 Four Continents Championships, they were third after the short program and then had a personal best score in the free skate to win the gold medal, the first American team to do so in over a decade.

[15] As a result, they withdrew from the World Championships, and were replaced by bronze medalists Deanna Stellato / Nathan Bartholomay.

At the 2018 Internationaux de France, Kayne/O'Shea were fourth after the short program, but placed second in the free skate, finishing less than two points ahead of bronze medalists Aleksandra Boikova / Dmitrii Kozlovskii.

Kayne remarked that after a "less than desirable" performance in Japan, "to have come to France and make this much improvement in just two short weeks made us both very happy.

In the free skate, they made some small opening mistakes on their twist and side-by-side jumps, but then had a major error when they failed to execute their final lift, which caused them to drop to fourth place.

They competed at the 2020 Skate America, primarily attended by American pairs teams due to travel restrictions relating to the COVID-19 pandemic.

Kayne was one of several skaters to file complaints against Sappenfield with the United States Center for SafeSport, leading to her suspension pending further investigation.