This article aims to explore and contest the various aspects of theoretical framework and practice of John Shakespeare (1774–1858) resorted to while compiling Urdu-English dictionary. John Shakespeare's Urdu-English dictionary, A Dictionary Hindustani & English, with copious index fitting work to serve also as Dictionary English and Hindustani is deemed one of the most important dictionaries compiled by those European scholars who happened to serve East India Company. Their dominant perspective has been pragmatic, aligned with the common imperial paradigm enunciated as ‘knowledge is a power’. Besides including a comprehensive introduction of the distinguished lexicographer, an analysis of the relationship between Orientalists’ Urdu-English lexicography and the East India Company has been carried out. In a bid to highlight the defining features of John Shakespeare’s dictionary, a comparison with the skills, preferences and methods employed in the dictionaries of his predecessor Joseph Taylor (1668-1798) and successor Duncan Forbes (1798-1868) has been drawn. In addition, a brief debate on the significance of Karkhandari language (dialect of Delhi Urdū) is added.