Dilip started acting in 1980 joining Sangit Kala Mandir (Kolkata). His first play was Thank You Mr. Glaad (Dir: Mrs. Geeta Jani). He then was part of Anamika, Prayaas, Rangkarmee, Spandan and then joined Padatik in 1998. He has acted in plays like Kauva Chala hans ki chaal (Dir: Late Shyamanand Jalan), Hidden Fires (Dir: Jayant Kripalani), Mantri Mandal (Dir: Sri Ashok Singh), Yeh zindagi aakhir kiski, Wada Chirebandi, Thaneer Thaneer, and Late Lateef (Dir: Late Kunal Padhi), Badal Sircars Saari Raat, Pagla Ghora (Dir: Sheo Kumar Jhunjhunwala) and other plays with different groups. Dilip has also acted in Gujarati plays like Aswathama and Trikon (bagged best actors award, play selected for DD Bangla). He has also acted in English and Bengali plays along with having dabbled in Bengali/Hindi TV serials and films.