[10][note 1] In the 2014 season she won the Grade-2 Bratislava tournament, defeating Slovakian Viktória Kužmová, who later became her doubles partner in senior events.

She finished her doubles junior career by taking the title at the 2016 Australian Open, winning with Slovak player Tereza Mihalíková.

[14][note 1] Her third ITF title of the year came in July at a $25k event in Aschaffenburg in Bavaria, Germany where she bested Dalila Jakupović in a three-set match.

At the Kremlin Cup, she made her WTA Tour debut, after receiving a wildcard for the third year in a row, but this time in the main draw.

[14][note 1] Kalinskaya started the year as a top 200 player, making her Grand Slam debut in qualifying at the Australian Open.

[17] In early March, at the Malaysian Open, she recorded her first tour-level main-draw win, defeating French top-30 player Caroline Garcia in straight sets.

She played in China at two $60k tournaments: first destination was Zhuhai where she was eliminated in the first round by former top-10 Swiss player Patty Schnyder before she headed to Shenzhen where she reached semifinals, but lost to compatriot Ekaterina Alexandrova.

At the French Open, she notched her Grand Slam debut in doubles, but lost in the first round with fellow Russian Ekaterina Makarova.

[30] In August, Kalinskaya showed an impressive North American hardcourt swing, reaching the semifinals of a WTA Tour event for the first time in her career at the Washington Open.

She survived the qualifying rounds, before making a huge comeback against reigning Puerto Rican Olympic champion Monica Puig, and stunning Mladenovic for her first win over the Frenchwoman in three attempts.

[34] Another tour quarterfinal soon followed in late September at the Tashkent Open, where she beat German player Tatjana Maria en route.

[37] Before the pandemic forced the cancellation of the tennis season in March, Kalinskaya lost in the first round of the Mexican Open, followed by another first-round loss, this time at the WTA Challenger Indian Wells.

This was her first time in the main draw of a Premier 5/Mandatory tournament, but she fell in the first round to Czech player Marie Bouzková, in straight sets.

[14][note 1] At the US Open, Kalinskaya beat Serbian Nina Stojanović to reach the second round for the second consecutive year, but lost to Czech 20th seed Karolína Muchová.

Her season began with the Premier Gippsland Trophy as part of the Australian Open warm-up, but she was eliminated in the first round by Katie Boulter.

She started well, winning her first match, but was unable to qualify for the main draw when she lost to French player Clara Burel in three sets.

[14][note 1] Following these weak performances, she began a resurgence at the Monterrey Open, reaching the quarterfinals as a qualifier after beating second seed Nadia Podoroska of Argentina in the first round.

[38] Her run continued the following week as a wildcard at the Miami Open, where she reached the third round of a WTA 1000 tournament for the first time in her career, and lost to 12th seed Garbiñe Muguruza, despite leading 3-0 in the deciding set.

151 in the singles rankings in October,[13] Kalinskaya returned with a fourth-round appearance at the Indian Wells Open as a qualifier, scoring her third top-50 win of the year over Sara Sorribes Tormo of Spain in the process.

The following week she qualified for the main draw at the Kremlin Cup, but was forced to retire in the second round against Greek player Maria Sakkari due to an injury.

[43] The Yarra Valley Classic was her first doubles event of the year, and she made it into the final alongside Kužmová, before losing to the Japanese duo of Ena Shibahara and Shuko Aoyama.

[47] The second good result came at the Indian Wells Open, where she won two qualifying matches and achieved main-draw wins against two French players, Harmony Tan and Alizé Cornet.

[14][note 1] The same situation happened again at the Miami Open, where she reached the third round after qualifying, but this time she did a walkover before the third-round match against Lucia Bronzetti.

[76] Moving on to the clay-court swing, Kalinskaya defeated qualifier Clara Tauson[77] at the Italian Open, before going out in the second round to 16th seed Elina Svitolina.

[88] At the WTA 1000 Canadian Open, she overcame qualifier Louisa Chirico[89] and Lesia Tsurenko[90] to reach the third round where she retired with an injury, after losing the first set to Amanda Anisimova.

There she defeated lucky loser Priscilla Hon[102] and Yuan Yue[103] to make it through to her fourth WTA Tour quarterfinal of the season.

[105] Partnering Priscilla Hon, Kalinskaya was runner-up in the doubles at the Brisbane International, losing to Mirra Andreeva and Diana Shnaider in the final.

[106] The following week, at the Adelaide International, she retired due to injury while trailing in her first round match against seventh seed Belinda Bencic.

[108] Kalinskaya returned to action as top seed at the Singapore Open, where she recorded wins over Caroline Dolehide,[109] Simona Waltert[110] and Mananchaya Sawangkaew to reach the semifinals.

[114] Kalinskaya again represented Russia at the 2020 Billie Jean King Cup, helping her country get to the finals by winning the decisive doubles rubber with partner Anna Blinkova.