He undertook various musical studies at Stuttgart with Speidel and with Lebert and Pruckner. He studied composition at Franfort with Dr Hauff, and after staying there for six months moved on to Florence, Italy, where he studied singing with Vanuccini. Study in operatic composition followed, first with Richard Genée, in Vienna, and then with Léo Delibes, in Paris.
De Koven returned to the US in 1882 to live in Chicago, Illinois, and later lived in New York. He was able to find scope for his wide musical knowledge as a critic with Chicago's Evening Post, Harper's Weekly and New York's World. Many of his songs became popular, especially "Oh, Promise Me", which was one of the biggest song successes of its time. His comic operas were popular, and as a composer of works of this description De Koven, like Victor Herbert, become famous throughout the country. His greatest successes include Robin Hood, produced in Chicago, 1890, and in London, 1891, Rob Roy, produced in Detroit, 1894, The Mandarin, produced in Cleveland, Ohio in 1896 and The Highwayman (1898). Harry B. Smith wrote many of the libretti for his operettas. His opera The Canterbury Pilgrims premiered at the Metropolitan Opera in 1917.
From 1902 to 1904 he conducted the Washington, D.C. symphony. His wife, Anna de Koven, was a well-known socialite, novelist and amateur historian who published her works under the name "Mrs. Reginald de Koven."