 He signed a new one-year contract with Leicester in June 2008.Pentney joined Woking on a one-month loan on 23 October and he finished this spell with two appearances.He made his first team debut for Leicester after coming on as a 59th minute substitute for David Martin against Swindon Town in a League One match, where he made saves against Simon Cox and Hal Robson-Kanu as Leicester drew 1–1.