Conrad Riley was born in England and immigrated to Canada when he was an infant. Riley’s interests included trapshooting, horseback riding, polo, hockey, curling, and duck hunting. When he was 17 years old, Riley took part in the sport of rowing which soon bypassed his other activities and, in 1893, he became a member of the Winnipeg Rowing Club (WRC).

By 1900, Riley had developed into a skilled oarsman and was named vice captain of the WRC. In 1902, Riley went to the U. S. National Championships in Philadelphia where the Winnipeg crews won both the intermediate and senior eights events. The WRC sent a crew to the 1904 Royal Henley Regatta in England, which is one of the world’s most prestigious annual rowing competitions. With Riley in the bow position, the Winnipeg crew finished second to the Third Trinity crew from Cambridge University, England. In 1910, the WRC returned to the Henley, defeated the prominent and favourite English in the preliminaries, and went on to race a team from Mainz (also known as Mayence), Germany, for the championship. The Winnipeg “Colonials” beat the German crew to take the Stewards' Challenge Cup which symbolized Henley supremacy.

In 1912, Riley led fourteen members of the Winnipeg Rowing Club at the National American Championships (N.A.A.O.) Regatta. The Winnipeg crews captured every race and achieved the first clean sweep at the N.A.A.O. Immediately prior to the Great War, a Winnipeg crew that included Riley faced the American Harvard team for the Grand Challenge Cup at the Henley but the Canadians were defeated by 3/4 of a length. In 1914, Conrad Riley retired from competitive rowing. He enlisted in the armed forces’ Artillery division during the war and upon his return to Canada became active in his father’s business. Conrad Riley was posthumously inducted into Canada’s Sports Hall of Fame.