Their first important commission was the main YMCA for Richmond, Virginia (1885–87), designed in a Richardsonian Romanesque style.
Their earliest major Collegiate Gothic building was Radnor Hall at Bryn Mawr College, built in 1886, where they replaced Cope's mentor Addison Hutton as campus architects.
The firm designed Philadelphia buildings for the Harrison brothers, heirs to an enormous sugar-refining fortune.
Charles Custis Harrison became provost of the University of Pennsylvania in Philadelphia in 1894, and immediately removed Frank Furness as unofficial campus architect, replacing him with Cope & Stewardson.
The firm also collaborated with architects Wilson Eyre and Frank Miles Day on the initial phases of the Arts & Crafts-style University of Pennsylvania Museum of Archaeology and Anthropology (1895–99).
In 1923, the annual T-Square club exhibition catalog published a photograph of the Cope & Stewardson office from about 1899.
Included among the partners and younger architects were: Walter Cope, John A. MacMahon, James O. Betelle (later of Newark, New Jersey); Emlyn Stewardson, S. A.
Cloud, Wetherill P. Trout, Herbert C. Wise, James P. Jamieson, Eugene S. Powers, E. Perot Bissell, Louise Stavely, Charles H. Bauer (later of Newark, New Jersey), William Woodburn Potter, John Molitor, Camillo Porecca, and C. Wharton Churchman.
Cope was also part of the investigating committee appointed to study conditions governing the new State Capitol Building competition in 1901.
They were joined in 1887 by John's younger brother Emlyn L. Stewardson, who had recently graduated from the University of Pennsylvania with a degree in civil engineering.
Stewardson died in 1896 after a skating accident on the Schuylkill River, where he had gone for an afternoon's outing with his friend, the architect Wilson Eyre.