In July 2016, Tomova reached the biggest final of her career so far at the Hungarian Ladies Open, losing to fellow Bulgarian Elitsa Kostova.

In October, she managed to qualify for the Linz Open, where she lost to the previous year's finalist Viktorija Golubic in three sets.

Tomova made her debut in the main draw of a Grand Slam tournament, coming through qualifying rounds at the Australian Open as a lucky loser, but then lost in straight sets to Nicole Gibbs.

She made her main draw debut at Wimbledon, going through qualifying and defeating wildcard Tereza Smitková for her first Grand Slam match win but then lost to Serena Williams in the second round, in straight sets.

Tomova made her WTA 500 main draw debut by reaching the second round with a win over Alizé Cornet at the 2019 Pan Pacific Open but was defeated by top seed and eventual champion, Naomi Osaka.

In April, Tomova reached for the first time in her career the semifinals of a WTA 250 tournament at the Copa Colsanitas with a three-set victory over Nuria Párrizas Díaz.

In August, Tomova entered the main draw of her first Grand Slam tournament for the season, coming through qualifying rounds at the US Open as a lucky loser where she lost to Lauren Davis.

Tomova qualified for the Australian Open to make her second main draw at this major but lost to eventual first-time quarterfinalist Alizé Cornet.

Also at the French Open, she made her debut as a lucky loser, thus completing the set of main-draw appearances in all four Grand Slam events.

69 and second seed, Varvara Gracheva, en route, before losing in three tight sets to eventual finalist Wang Xiyu.

37, Shelby Rogers, and then advanced to her first WTA 500 quarterfinal after defeating Kirsten Flipkens and taking revenge for the loss in the final round of qualifying.

[24] She qualified for the main draw at the Ladies Linz defeating Barbara Haas and former French Open finalist, wildcard Anastasia Pavlyuchenkova.

[26] Next, she qualified again this time for the main draw of the WTA 500 in Doha defeating three players in the top 100, Maryna Zanevska and two Americans, Lauren Davis and Madison Brengle.

[29] The following week, she reached again the main draw after qualifying at the WTA 1000 Dubai Championships defeating Ankita Raina and Jang Su-jeong.

At the next WTA 1000, on her Miami Open debut, she entered the draw as a lucky loser[32] and defeated fellow qualifier Anna Karolína Schmiedlová in the first round before she lost to 30th seed Danielle Collins.

In April, she reached the final[33] and won the title at the $80k tournament in Zaragoza[34] defeating fourth seed Tereza Martincová.

As a result of winning her biggest title since 2019, she moved to a new career-high in the top 75 and became the first Bulgarian since Tsvetana Pironkova in 2017 to reach this ranking.

[41] She won the biggest title of her career at the WTA 125 Chicago Challenger defeating American Claire Liu in straight sets.

[42][43][44] Tomova entered her first tournament of the season, the Hobart International as a lucky loser and defeated Martina Trevisan in straight sets.

[45] She then defeated ninth seed Tatjana Maria[46] to advance to her first hardcourt quarterfinal in which she lost to eventual champion Emma Navarro.

[47] The following week at the Australian Open, Tomova won her first match at this major defeating Kayla Day,[48] She lost to 19th seed Elina Svitolina in the second round.

[51] At the WTA 1000 Miami, she defeated lucky loser Tamara Korpatsch,[52] before retiring due to a back injury while trailing in her next match against 23rd seed Caroline Garcia.

[55] In May at the Morocco Open in Rabat, she reached her third tour semifinal defeating qualifier Berfu Cengiz,[56] Wang Yafan[57] and Laura Siegemund,[58] before losing to Peyton Stearns in three sets.

[64][65] At the WTA 500 Bad Homburg Open, Tomova qualified for the main draw and reached the round of 16 by defeating Tatjana Maria in straight sets.

[80][81][82] She reached the quarterfinals with a win over Amanda Anisimova, after her retirement in the second set with Tomova leading 7–5, 4–1,[83] but ultimately lost to Veronika Kudermetova.

In doubles at the same tournament, she also reached the quarterfinals with her partner Makoto Ninomiya but lost to top seeds Chan Hao-ching and Kudermetova.

[84][85][86] On her debut at the China Open, Tomova defeated Lesia Tsurenko in straight sets,[87] before losing to 15th seed Paula Badosa.