[6][7][8] Initially promoted as the carbon copy of Satabdi Roy, Sengupta made her screen debut opposite Kushal Chakraborty in the Bengali fantasy TV series Shwet Kapot (1989) directed by the latter and broadcast on DD Bangla.

[9][10] She made her big screen debut opposite Bijay Mohanty in the Odia film Kotia Manish Gotiye Jaga (1991) directed by Vijay Bhaskar.

[11][12] Throughout her career, she featured in a host of National Award-winning Bengali films such as Shwet Patharer Thala (1992), Lathi (1996), Dahan (1997), Paromitar Ek Din, (2000), Mondo Meyer Upakhyan (2002) and Anuranan (2006).

[14] Sengupta made her screen debut opposite Kushal Chakraborty in the Bengali fantasy TV series Shwet Kapot (1989) broadcast on DD Bangla.

[24][23] Sengupta auditioned for the role of Radha in Vijay Bhaskar's Odia film Kotia Manish Gotiye Jaga (1991) and was selected.

Her father Prabir Sengupta initially disapproved the film as she was required to enact a bathroom sequence alongside Mohanty.

After Gargi Roychowdhury declined the role of Titli opposite Bhaskar Banerjee in Prabhat Roy's National Award winning Bengali film Shwet Pathorer Thala (1992), Sengupta was offered to play the character.

She featured opposite Prosenjit Chatterjee in Vijay Bhaskar's Nag Panchami (1994)[31] and Chiranjeet Chakraborty in Prashanta Nanda's Laal Paan Bibi (1994).

[32] Sengupta made her Hindi cinema debut opposite Chunkey Pandey in Partho Ghosh's thriller Teesra Kaun (1994) which was a debacle at the box office.

[37] 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.

In the second year of Shakib Khan's career in 2000, she collaborated with him for the first time in FI Manik's action Palta Hamla: The Counter Attack.

[42][43] Swapan Saha cast Sengupta alongside Abhishek Chatterjee, Tapas Paul and Satabdi Roy in his family drama Sukh Dukkher Sansar (2003).

[44] In 2004, Sengupta had 1 Odia Film Katha Deithili Maa Ku with Sidhant Mohapatra only successful Venture of 2004, all other 12 releases in Bengali cinema, all of which became box office debacles generating the common notion among the filmmakers that the actress had lost her market value.

[45] Sengupta starred in Sushanta Saha's Sagar Kinare (2004) where she shared silver screen with Debashree Roy for the first time.

She featured opposite Rajpal Yadav in Chandan Arora's critically acclaimed Main, Meri Patni Aur Woh (2005).

She featured opposite Tapas Paul in Satabdi Roy's Om Shanti (2012) that also stars Rakhi Sawant in a dance number.

[66][67][68][69] In Kamaleshwar Mukherjee's Goodnight City (2018) she featured as psychiatrist Abhiri Chatterjee who implores her husband who is a deputy commissioner with the detective department, not to be hard on the protagonist, a murderer whom she believes to be a psychologically distraught person.

The Times of India wrote on her performance, "she shows the compassionate side of her character nicely, the unemotional and professional psychiatrist goes missing every now and then.

[78] In Reshmi Mitra's Lime N Light (2019) she enacted double roles of Sreemoyee Sen, an actress and Archana Saha, a junior artiste.

[83] The Times of India wrote in their review, "Rituparna gives Arifin and Paran Bandopadhyay a run for their money with her mature, measured performance as Basundhara — a woman whose past grief pushes her to put her heart and soul into cooking and caring for her family of three.

Her Basundhara is a woman who does not wear her emotions on her sleeves, but there is a scene towards the end of the film, when she can't take it anymore and just breaks down.

[85] Asianmoviepulse.com wrote in their review: "Rituparna Sengupta is a splendid actor and portrays the character of Basundhara with subtle emotional traits.

Rituparna Sengupta is a strange mix of someone resigned to her fate in some matters, and at the same time, someone who can go to any extent to prevent any harm that might come to her family.

[87] Rossini Sarkar from Cinestaan wrote in her review: Rituparna Sengupta carries the film on her shoulders, gradually creating her state of depression through perpetual tension, unreasonable outbursts and a haggard look.

[89] Sengupta starred in the role of Bijaya in Nirmal Chakraborty's Datta based on Sarat Chandra Chatterjee's novel of the same name.

[93] The relationship between the two got sour during the shooting of Prashanta Nanda's Laal Paan Bibi (1994) when Sengupta literally broke drown into tears after she was denounced for coming late to the set of the film, by Roy who was the bigger star by then.

[94][95] In August, 2023, at the press conference of Anonno Mamun's new film Sporsho, Sengupta was interrogated by a Bangladeshi journalist how she can manage to portray the romantic lead opposite a much younger hero at the age of 52.

[99] On 19 July 2019, Sengupta was interrogated by ED officers about an amount of near about 7 crore that she had received from the Rose Valley Group led by Gautam Kundu.

On 15 August 2024, Sengupta posted a video of blowing out a conch shell in favour of justice for the victim of the 2024 Kolkata rape and murder.

[103][104] Sengupta joined Reclaim the Night movement but had to leave abruptly as she was denounced by the mob who raised 'go back' slogan against her.