In February, Olmos and Canadian player Sharon Fichman reached their first Grand Slam quarterfinal at the Australian Open, and in April she partnered with another Canadian, Gabriela Dabrowski, to reach the semifinals of another WTA-1000 tournament at the Miami Open. In May, Olmos won the biggest title in her tennis career at the WTA 1000 Italian Open, partnering with Fichman; in the final, they defeated the pair of Kristina Mladenović and Markéta Vondroušová who were making their debut playing together. They entered the tournament as alternates and defeated top seeds Hsieh/Mertens and the Japanese fourth-seeded duo Aoyama/Shibahara en-route to the championship match. As a result, she entered the top 30 in doubles for the first time in her career.
Parry has a career-high ITF junior combined ranking of world No. 1, attained on 21 October 2019. She was designated ITF Junior World Champion for 2019. She made her WTA Tour main-draw debut at the French Open thanks to a wildcard, partnering Giulia Morlet; they were defeated by the 13th-seeded pair of Kiki Bertens and Johanna Larsson, in two sets in the first round.