In 1992, Maleeva snatched her first WTA Tour event victory in San Marino and scored her best Grand Slam tournament result with a quarterfinal run at the US Open, upsetting Martina Navratilova on the way.

Her best performance at a Grand Slam championship came when she got to the quarterfinals of the 1992 US Open, defeating Kateřina Kroupová-Šišková, Martina Navratilova, Kimberly Po and Chanda Rubin before losing to her older sister Manuela.

In 1995, Maleeva won a total of three tournaments, in Moscow, Chicago, Oakland, which saw her hit a career-high ranking of No.

In 2002, she won the prestigious Kremlin Cup in Moscow, defeating three top-10 players on her way (Venus Williams, Amélie Mauresmo, and Lindsay Davenport).

In 2011, she made a brief tennis comeback, playing and winning three doubles matches for Bulgaria at the Fed Cup.

[2][3] In March 2011, Maleeva was voted eighth in the "100 most influential women in Bulgaria" by Pari newspaper.

She has also appeared at Wimbledon's ladies' invitation doubles event on several occasions, achieving her best result in 2015, where she partnered Rennae Stubbs; the pair defeated Navratilova and Selima Sfar in the final to win the title.