In 1999, Matondkar had six film releases; four of them − Jaanam Samjha Karo, Hum Tum Pe Marte Hain, Mast and Dillagi − were critical and commercial failure . However, Matondkar's performance was generally well received by critics, (Rediff describing "Urmila is just about the only heroine who can give Karisma a run for her money when it comes to pelvic thrusts"). Her first hit that year was Ram Gopal Varma's thriller film Kaun, opposite Manoj Bajpai, in which she played the Nameless character. Khalid Mohamed of The Times of India (who would later cast her in Tehzeeb) wrote that she "rivets the viewer's interest, carrying off entire reels on her shoulders, through a gamut of quicksilver facial expressions. Vulnerable and baffled, she is utterly believable as the traumatised girl-next-door". Matondkar next played the love interest of Sanjay Dutt's character in the hit action comedy Khoobsurat.