In his second match back, on 17 January 2009, Randolph conceded four goals in a Championship match against Sheffield Wednesday. This was to be his last appearance of the season. Nevertheless, he was offered, and eventually signed, a one-year contract ahead of the 2009–10 season.</ref> He was again second choice, this time behind Rob Elliot, and made his first appearance of the season in November, in the FA Cup against Northwich Victoria. Despite "a string of stunning first half saves", the Conference North team won 1–0 to inflict what the local newspaper described as the "most embarrassing defeat in the club's 104-year history". Randolph regained his starting place in March 2010 after Elliot was injured, and kept it for the remainder of the season, including the play-offs, in which Charlton lost on penalties to Swindon Town in the semi-finals.