In 2004, she got critical recognition for her performance as a merciless avenger in Ram Gopal Verma's Ek Hasina Thi, co-starring Saif Ali Khan. She played the role of a deceived woman who is jailed because of her lover, played by Khan, and later flees from prison to avenge him. Once again, Matondkar was nominated for a Filmfare for her performance in the film.
Next year in 2005, she tried her hand with another horror film, playing the title role in the film Naina, which failed. However, her performance as the caring daughter of Anupam Kher in Jahnu Barua's art film Maine Gandhi Ko Nahin Mara was very well received, and she won her second Bollywood Movie Award for Best Actress.
Apart from holding a successful acting career, she is regarded as an outstanding dancer and has been a featured performer in many Bollywood item numbers. Her best-known item number is the Chamma Chamma sequence from the 1998 China Gate. Other hit numbers include Aaiye Aajaye from the hit film Lajja. She was signed to perform the item song in Ram Gopal Varma Ki Aag, a remake of the 1975 blockbuster Sholay. She played the role originally played by Helen.
In 2007, Matondkar lent her voice for Asha Bhonsle's album Asha and Friends Vol 1, where she performed with Bhosle the duet song "Mehbooba Dilruba". In fact, throughout the 1990s – 2000s, Bhosle sang the maximum number of songs for Urmila.
In 2008, Matondkar was seen with Himesh Reshammiya in a remake of the 1980 film Karz, Karzzzz. 2008 also marked Matondkar's debut on Indian television as a host of a reality show named Waar Parriwar.
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