In January 2014, after repeating as national silver medallist at the Canadian Championships, she was named in Canada's team to the 2014 Winter Olympics in Sochi in February.

[14] Competing on the Grand Prix series, she placed fifth at the 2015 Skate Canada International and sixth at the 2015 Trophée Éric Bompard.

She won the silver medal at the 2016 Canadian Championships in Halifax, Nova Scotia, finishing behind Alaine Chartrand and ahead of Kaetlyn Osmond.

In the 2015–16 season, Daleman adjusted several aspects of her training and preparation – to practice elements with the same entry and exit as in her programs, improve the precision and timing of her in-between movements, and work more regularly with a mental performance consultant for athletes.

[16] Daleman took the bronze medal at the 2016 CS Nebelhorn Trophy, behind Mai Mihara and Elizaveta Tuktamysheva, before appearing in her third Grand Prix series.

At her next GP event, the 2016 Trophée de France in Paris, she placed second in the short program, sixth in the free skate, and fourth overall.

In January 2017, Daleman won the silver medal at the 2017 Canadian Championships, finishing second to Kaetlyn Osmond with a deficit of 8.57 points.

[17][18][5] In early November, Daleman finished sixth at the 2017 Cup of China after winning the short program and placing seventh in the free skate.

Daleman's free skate proved difficult, characterized by The Toronto Star as "a shambles" that featured "three falls, two over-rotations, a doubled-down triple" and "an agonizingly slow camel spin."

[21] Daleman fell and hit her head during training before her first event of the season, the 2018 CS U.S. International Classic; she did not report the incident, believing that she was not injured.

After returning to Toronto, she developed a series of health problems – including pneumonia, strep throat, anxiety, depression, a severe headache, and blurry vision – then collapsed and lost consciousness for a few seconds while at home; a doctor attributed this fall to a concussion, which most likely occurred when she hit her head before the U.S.

[24] Returning to competition, Daleman placed first in the short program at the Canadian Championships, declining to speak to the media until the event was over in order to manage her mental health.

[27] Daleman placed eleventh in the short program, skating cleanly but for a slightly negative Grade of Execution on her triple Lutz.

This result, combined with that of Alaine Chartrand, preserved Canada's second spot for the 2020 World Championships to be held in Montreal.

Daleman commented afterwards that despite multiple jump errors in the free skate, she was pleased with how the event had gone, saying, "I had the worst two years of my life and to be here and get a top-12 finish means the world to me.

She went on to skate the free, placing tenth after multiple falls, but discovered upon returning home that she had cracked two ribs and sustained another concussion and a serious bruise on her knee that necessitated using a cane.

"[31] Two weeks later, Daleman competed at 2019 Skate Canada International, placing fifth in the short program with only a minor error on her triple flip.

[33] After withdrawing from the Cup of China, Daleman tore two ligaments in her ankle and strained her Achilles tendon, necessitating over a month spent off the ice.

[38] With the COVID-19 pandemic severely curtailing the figure skating season, fall international assignments were unavailable to Canadian skaters, and domestic competitions were not held in person.

[47] Despite numerous jump errors, Daleman won the bronze medal at the 2022 Canadian Championships, placing third in both segments of the competition.

[50] After missing the Challenger series due to injury, Daleman made her season debut at the 2022 Skate Canada International, where she unexpectedly finished second in the short program, behind only fellow Canadian Madeline Schizas.