Born on 12 May 1987 in Bray, Republic of Ireland, Randolph joined Ardmore Rovers in 1998 before moving to Charlton Athletic in 2003, where he turned a full professional in 2004.
However, he could only manage to feature in 14 leagues between 2004 and 2010. Nevertheless, he had loan spells between that same period at Wellington United, Accrington Stanley, Gillingham, Bury, and Hereford.
On 1st July 2010, he moved to Scottish league outfit, Motherwell on a free transfer. During his three year stint at the club, he played 136 games, kept 43 clean sheets and conceded 172 goals. In July 2013, Randolph signed a two-year contract with English Championship side Birmingham City, where he was nearly an ever-present figure for the side, raking up 92 appearances in his two years stay at St. Andrew's.
Randolph moved to West Ham United in the summer of 2015 and played 42 games. He was in goal for the Hammer's 3-2 victory over Manchester United, which was West Ham’s final game at the Boleyn Road stadium.
The Republic of Ireland international has featured at all levels and was signed by Middlesbrough FC on a four-year deal worth £5 million in 2017. In his first season at the Riverside, he played every league game, and he did the same in the second season, featuring in all 46 league games for two consecutive seasons.
July 2017 - June 2021
July 2015 - July 2017
July 2013 - June 2015
July 2010 - June 2013
November 2008 - June 2010
July 2008 - November 2008
September 2006 - June 2008
August 2006 - September 2006
November 2005 - August 2006
August 2005 - November 2005
July 2005 - August 2005