Orth played for the Philadelphia Phillies in his first seven seasons (1895-1901), where he won an even 100 Games against 72 Losses. He led the National League in WHIP (1.001) and BB/9 (1.0), and the season after, when he joined the Washington Senators, he again led his new league in BB/9 (1.1). Notably, Orth finished in the top ten in BB/9 nine times. After two years in change with the Washington Senators, he was traded during the 1904 campaign to the New York Highlanders, and with the team that would eventually become the Yankees, he had a league-leading 27 Wins in 1906. That was Orth's last good year, as skills tapered off, and he was out of the Majors in 1909.
Despite having a bWAR over 50 and more than 200 Wins, Orth never appeared on a Hall of Fame ballot.