At 22 years of age, Evans was the youngest umpire in major league history; furthermore, he was among those very rare umpires who broke into the major leagues with little previous professional experience. He was regarded as the only umpire of his era who never had played professional baseball himself. After making his debut at Highlanders' Park in New York City, he went on to umpire for six World Series: 1909, 1912, 1915, 1917, 1919 and 1923. Working in an era during which most major league games used no more than two umpires (and sometimes only one), Evans single-handedly umpired seven double-headers in eight days during the 1907 season. He was the base umpire for Charlie Robertson's perfect game on April 30, 1922.