He began his professional career at his local team Middlesbrough, going on to depart on eight individual loan spells. These included multiple spells at various English clubs as well as Motherwell in Scotland and Östersund in Sweden. During this time, he represented England at under-19 and under-20 levels.
Ripley began his career with Blackburn Rovers. After moving to Middlesbrough in 2009, he signed a two-and-a-half-year professional contract in January 2011. Ripley made his professional debut on 5 March 2011 in a 5–2 loss to Reading, conceding three goals after coming on as a substitute for Jason Steele. Ripley made his full debut on 14 January 2012, in a 2–0 loss at home to Burnley.
He then went out on an emergency loan to Oxford United, after both their goalkeepers had suffered injuries. Ripley made his only appearance for Oxford United, in which he conceded a goal from Ryan Hall‘s free kick, in a 2–0 loss against Southend United the next day. After this, manager Chris Wilder was unhappy with Ripley’s performance and decided to terminate his loan spell at the club. After returning to Middlesbrough, Ripley became the third-choice goalkeeper around the 2012–13 season and in January 2013 signed a new contract with the club.