She has an aggressive style of play, and possesses the ability to hit powerful groundstroke winners, especially on the forehand side.

Dolehide attended Hinsdale Central High School until her sophomore year, when she moved to Florida to train with the United States Tennis Association (USTA).

Dolehide had verbally committed to play tennis at UCLA, but ultimately decided to forgo attending college to pursue a career as a professional.

She upset three of the top ten seeds in the tournament, including Markéta Vondroušová in the first round, before losing to the eventual champion Marie Bouzková.

[8] Later that year, she also made it to the semifinals of the Eddie Herr Championships and the quarterfinals at the Orange Bowl, two prestigious Grade 1 tournaments.

[12][13] Dolehide began playing regularly on the ITF Women's Circuit in 2016, after missing the second half of 2015 with a broken left foot.

[21] A few weeks later, Dolehide followed up this performance by winning a 100k title at the Abierto Tampico with veteran María Irigoyen,[22] a victory that helped her finish the year just inside the top 100 of the WTA doubles rankings.

[23] In March 2018, Dolehide was awarded a wildcard into the main draw of the Indian Wells Open, where she picked up her first two match wins at a Premier Mandatory tournament, including a second round victory over No.

[24][25] Dolehide continued her momentum into the clay-court season, where she won the $60k event at Indian Harbour Beach, the biggest title of her career.

In her Grand Slam main-draw debut in singles, Dolehide defeated Viktorija Golubic before losing to Madison Keys in the following match.

She finished runner-up at Bonita Springs in Florida with Usue Maitane Arconada, before winning a title at the Surbiton Trophy with Jennifer Brady.

[23] Her form began to rebound in a big way after she brought back two medals from the 2019 Pan American Games in Lima, Peru.

The pair reached semifinals, defeating the 14th-seeded team of Lyudmyla Kichenok and Jeļena Ostapenko, before losing to the eventual champions Elise Mertens and Aryna Sabalenka.

[23] Dolehide won her maiden WTA Tour doubles title, partnering Asia Muhammad at the 2021 Monterrey Open where they defeated Heather Watson and Zheng Saisai in the final in straight sets.

206, she reached her second WTA Tour-level quarterfinal at the 2023 Monterrey Open as a qualifier defeating Jule Niemeier and Anna Karolína Schmiedlová and her first since Québec City in 2017.

She reached the round of 16 at the Charleston Open defeating Sabine Lisicki[33] and Linda Fruhvirtová, before losing to eventual champion Ons Jabeur.

[39][40] With her win over Sofia Kenin and reaching the final, she also became the second lowest ranked finalist (after Kuznetsova) at a WTA 1000 level since the introduction of the format in 2009.

[46] At the same tournament, immediately following her singles quarterfinal match, she also reached the semifinals with Asia Muhammad defeating Miyu Kato and Aldila Sutjiadi in one hour.

[47] At the French Open, she reached the semifinals for the first time at this tournament with Krawczyk but lost to Coco Gauff and Katerina Siniaková.

[50] At the Birmingham Classic, where she entered the main draw as a lucky loser, she defeated Karolína Plíšková saving two match points,[51][52] and fifth seed Elise Mertens by retirement to reach the quarterfinals[53] where she lost to eventual champion Yulia Putintseva.

[55][49] In the beginning of the American summer swing, at the WTA 500 Washington Open, Dolehide defeated Lesia Tsurenko,[56] second seed Daria Kasatkina[57] and Amanda Anisimova[58] to reach the semifinals where she lost to eventual champion Paula Badosa.

[76] Partnering Desirae Krawczyk, Dolehide qualified for the end-of-season WTA Finals in Riyadh, Saudi Arabia, but they were eliminated in the group stages after losing all three of their matches.

"[79] Only main-draw results in WTA Tour, Grand Slam tournaments, Fed Cup/Billie Jean King Cup and Olympic Games are included in win–loss records.