Sengupta hit the pinnacle of her professional rivalry with Satabdi Roy in the late 1990s since the two were offered most of the female leads opposite Prosenjit Chatterjee after Debashree Roy vowed not to work with Chatterjee any longer. Sreelekha Mitra claimed that Sengupta had an extramarital affair with Chatterjee, which helped her get most of the female leads opposite Chatterjee. She featured opposite Chatterjee in a string of commercially successful Bengali films such as Abujh Mon (1996), Matir Manush (1997), Mayar Badhon (1997), Moner Manush (1997), Pabitra Papi (1997), Samadhan (1997), Tomake Chai (1997), Baba Keno Chakar (1998), Praner Cheye Priyo (1998), Daay Dayitwa (1999), Madhu Malati (1999), Sindur Khela (1999), Sudhu Ekbar Bolo (1999), Tumi Ele Tai (1999), Aasroy (2000), Madhur Milan (2000) and Sasurbari Zindabad (2000) to name a few.
