Born in a zamindar family of Jorasanko with extensive lands in Orissa. Educated in Sanskrit, Bengali, English. Married 1854. After wife's death, remarried and she survived him. In 1857 left school at age 16. Established Vidyotsahini Sabha in own house in 1856 where he began reading out essays he had written. 1857 established Vidyotsahini Theatre in his own house and enacted Venisamhara. Encouraged by its success, published translation of Vikramorvashi and staged it in 1858; in 1858 wrote Savitri-Satyavan; in 1859 Malati Madhava,. In 1861 took over editing of Hindu Patriot, Paridarshak and Vividhartha Sangraha.
Began translating Mahabharata into Bengali with a team of pandits in 1858. Completed in 1866. In July 1861 when Rev. James Long was fined Rs.1000/- for translating Nil Darpan Kaliprasanna deposited the entire amount in the court. Announced prizes for marrying widows and participated in agitations against polygamy and to shift prostitutes to other areas. Wrote a biting prose satire on society, Hutom Penchar Naksha(1862-64) which is important for using simple Bengali in literature instead of a language weighed down by Sanskrit words. Felicitated in Bengali Michael Madhusudan Dutt for his Meghnad Badh Kabya. Died aged only 29.
He dedicated his translation to Empress Victoria in gratitude for the British rescuing Bharatavarsha from the mortal clutches of the Mughals. He compares his offering to the gods offering the parijat flower churned out of the ocean to Purandara. The intention behind the translation was a faith that it would redound to the country's good. He trusts that Hindusthan will be lit up during her reign by hundreds of lamps of Sanskrit literature as during Vikramaditya's reign by Kalidas etc. and in Queen Elizabeth's reign by Shakespeare etc. to make her reign unforgettable.
He states that he engaged 7 pandits for the work, omitting and adding nothing. He excluded Harivamsa as he found its composition to be plainly later than the epic. He had a plan to publish its translation along with those of the Puranas. 3000 copies of each parva were printed, being unsure of the reception. What the editors of the critical text of the MBH have done now, Kaliprasanna Singha did in 1858, collating manuscripts from Asiatic Society, Sovabazar palace, collections of Asutosh Deb, Jatindramohon Thakur, and his own great grandfather Shantiram Singha's collection in Kashi. He acknowledges with gratitude the help he received in resolving contradictions in the texts and making out the meaning of knotty Vyasa-kuta slokas from Calcutta Sanskrit Vidyamandir's teacher Taranath Tarkavacaspati.
He records with profound gratitude that Ishwarchandra Vidyasagar began a translation of MBH and had published some parts of it in Brahmo Samaj's Tattavabodhini magazine, but stopped the work on hearing of Kaliprasanna's project. He not only went through Kaliprasanna's translation but whenever he was out of Calcutta, Vidyasagar supervised the printing and the work of translation in his absence. Kaliprasanna writes that he has no words to express the benefits Vidyasagar showered on him.
He gives special thanks to several friends viz. Michael Madhusudan Dutt for promising to turn the best parts of the translation into Amritakshar metre and a play; Purana expert Gangadhar Tarkabagish, Raja Kamalkrishna Bahadur, Jatindramohon Thakur, Rajendralal Mitra, Dwarkanath Vidyabhushan (editor of Somprakash), Rajkrishna Bandopadhyay professor of Bengali literature in Presidency College, Nabinkrishna Bandopadhyay former editor of Tattvabodhini, Dinabandhu Mitra the playwright of Nil Darpan, Kshetramohon Vidyaratan editor of Bhaskar. He deplores the death of 10 members of his team of translators and thanks those engaged till the end, viz. Abhaycharan Tarkalankar, Krishnadhan Vidyaratna, Ramsevak Vidyalankar, Hemchandra Vidyaratna and the proof readers (he mentions all their names). Daily at evening the translation as it progressed was read out to Raja Radhakanta Deb and other prominent leaders of Hindu society viz. Raja Kamalkrishna Bahadur, Rajkrishna Mitra. In villages, he writes, the translation is read out in important gatherings morning and evening. He pays a fulsome tribute to Kashiram Deb's translation in Bengali verse, regretting that details of his life and dates are not recorded anywhere. He leaves out discussion and summaries of Sanskrit literature based on Asiatic researches and Max Muller's edition of texts to avoid any controversy that might harm the unrestricted acceptance of his translation.