She garnered attention for playing the lead role of Zainab, a Muslim wife separated from her Sikh husband, in the 1999 Punjabi film Shaheed-e-Mohabbat Boota Singh, set against the backdrop of the 1947 Partition of India.

She followed this by playing the supporting role of Bindiya in the 1995 film Surakshaa, alongside Suniel Shetty, Aditya Pancholi, Saif Ali Khan and Sheeba.

In 1999, Dutta made her Punjabi debut in the romantic drama Shaheed-e-Mohabbat Boota Singh, in the first of her many roles opposite Gurdas Maan.

She played supporting roles in Shakti: The Power alongside Karisma Kapoor and Shah Rukh Khan, and in Sur – The Melody of Life.

In 2004, Dutta made her breakthrough in Hindi cinema with the role of Shabbo with Yash Chopra's epic love saga Veer-Zaara, alongside Shah Rukh Khan, Preity Zinta and Rani Mukerji.

Dutta was widely lauded for her performance, with Aakash Gandhi describing her as "doing a fantastic job serving as the maid who's trying to join the two lovers",[13] and critic Subhash K. Jha remarking that she "bring[s] enormous feeling.

That same year, she also appeared in supporting roles in Murder and Agnipankh, and collaborated for a third time with director Manoj Punj in the Punjabi film Des Hoyaa Pardes.

She also appeared in Silsiilay alongside Shah Rukh Khan and Bhumika Chawla, and in the comedy Mr Ya Miss.

[15] She also played the title role in Sanyogita: The Bride in Red, a Rajasthani girl struggling to control her desires in a patriarchal society.

In 2006, Dutta appeared in a small role in Darwaaza Bandh Rakho, alongside Aftab Shivdasani and Isha Sharvani.

"[18] Dutta made her international debut in the English Rituparno Ghosh film The Last Lear alongside Amitabh Bachchan, Preity Zinta and Arjun Rampal, playing the role of Ivy, a nurse.

Reviews of the film were mixed, but Dutta was mostly praised for her portrayal, with Aparajita Ghosh calling her "simply superb"[19] but Joxily John remarking that she is "wasted in a character that does not add any significant value to the proceedings.

She also appeared opposite Vinay Pathak in the comedy Oh, My God, which received mainly negative reviews, although Dutta's performance was branded "earnest.

[22] Dutta's first release of 2009, the Rakeysh Omprakash Mehra's drama film Delhi-6, was a box office flop and received mixed reviews.

She starred in Love Khichdi alongside Randeep Hooda and Avijit Ghosh of the Economic Times called her "among those who stand out.

In 2010, she appeared in the Punjabi film Sukhmani: Hope for Life, once again alongside Juhi Chawla and Gurdas Maan, playing the role of Reshma.

[29] The same year, she appeared in two international ventures- director Fred Holmes' multilingual project Heart Land[30] and the film Hisss alongside Mallika Sherawat.

The film received negative reviews and was criticised for underutilising her, with Taran Adarsh calling her "wasted"[31] and Pankaj Sabnani remarking that she "doesn't have much scope.

"[32] The following year, Dutta had nine releases, making appearances in Chaloo Movie and Masti Express, as well as the Punjabi film The Lion of Punjab.

"[34] However, her performance in the latter was met with mixed reviews, with Rediff stating, "Considering the oomph factor which Divya is capable of oozing on screen, it is one more opportunity lost as the all-pervading air is one of buffoonery,"[35] but with Jhinuk Sen calling her "rather endearing.

"[44] Her next release, the Madhur Bhandarkar drama Heroine also received negative reviews and had a below average performance at the box office.

However, her performance as Pallavi Narayan, the PR manager of a struggling actress, was highly praised, with Taran Adarsh commenting, "a special mention of Divya Dutta [in terrific form]"[45] and Lisa Tsering remarking "the supporting actors are strong throughout, especially the smart Divya Dutta as a wily PR maven.

"[47] Her next release was the drama Gippi, produced by Karan Johar, in which she played a single mother struggling with her victimised daughter.

Dutta then made an appearance in the period romantic drama Lootera alongside Ranveer Singh and Sonakshi Sinha.

The film, and her performance, were highly praised, with the Times of India branding her "outstanding,"[50] and Priya Joshi calling her "exceptional in a poignant role as his protective elder sister.

Her final release of the year was the political action thriller Zila Ghaziabad alongside Arshad Warsi and Sanjay Dutt.

The film received positive reviews and her performance as Anjali Mullati, the owner of a consulting company who decides to start fighting her own battle against the mafia, was praised, with Taran Ardash calling her "absolutely believable.