In 1920 he was appointed manager of Liverpool and in his first season in charge he guided them to their second successive season in 4th place, eight points behind the Champions Burnley.
The following season, 1921/22, Ashworth lead Liverpool to their third League Championship. The team were well on their way to a second successive Championship the following season, when in February 1923 Ashworth left the table-topping side to return to Oldham, then at the bottom of the league. Oldham ended the season relegated, while Liverpool only won one of their last seven games, but still won the Championship by six points.
Ashworth remained at Oldham for just over a year before moving to Manchester City, but he resigned in 1925 as the club struggled towards relegation. He next tried his hand in management with a brief spell with Walsall between 1926 and 1927.