Born in Providence, Rhode Island, Bennett graduated from Brown University in 1878 and also studied at Harvard (1881-1882) and in Germany (1882-1884). He taught in secondary schools in Florida (1878-1879), New York (1879-1881), and Nebraska (1885-1889), and became professor of Latin in the University of Wisconsin-Madison in 1889, of classical philology at Brown University in 1891, and of Latin at Cornell University in 1892. His syntactical studies, notably various papers on the subjunctive, are based on a statistical examination of Latin texts and are marked by a fresh system of nomenclature; he ranks as one of the leaders of the New American School of syntacticians, who insist on a preliminary re-examination of all available data.
Of great importance are his advocacy of quantitative reading of Latin verse and his Critique of Some Recent Subjunctive Theories in vol. ix. (1898) of Cornell Studies in Classical Philology, of which he was an editor. Bennett's Latin Grammar (1895) is the first successful attempt in America to adopt the method of the brief, scholarly Schulgrammatik. Besides the Latin classics commonly read in secondary courses and other text-books in Bennett's Latin Series, he edited Tacitus's Dialogus de Oratoribus (1894), and Cicero's De Senectute (1897) and De Amicitia (1897). He wrote, with George P. Bristol, The Teaching of Greek and Latin in Secondary Schools (1900), The Latin Language (1907), with William Alexander Hammond translated The Characters of Theophrastus (1902) and translated the Loeb Classical Library edition of the Odes and Epodes of Horace.
Foundations of Latin (1898)
Caesar's Gallic War (1903)
New Cicero (1922)