 Nyorai kuenderera mberi kwechikamu chino - Chester akaita Premier League yake yekutanga musi wa18 Nyamavhuvhu 2013 kuStamford Bridge mukukundwa neChelsea 2-0. Mitambo mishanu mumutambo wake wekutanga semutambi wechikwata chekutanga muPremier League, Chester akarambidzwa kwemasvondo matanhatu kusvika masere mushure mekudhonza hamstring yake vachipesana neNewcastle United musi wa21 Gunyana 2013. Mushure memwedzi miviri yekukuvara, akadzoka mukukunda kweHull 2-0 kure neArsenal musi wa4 Zvita. Chester akarova chibodzwa chake chekutanga mumwaka wa2013-14 muminiti yechina yemutambo weHull City weBoxing Day neManchester United; zvisinei, akazowana chibodzwa chechipiri-chechipiri kuti ape Manchester United kukunda 3-2. Musi wa17 Chivabvu 2014, akatanga mu2014 FA Cup Finalvachipesana neArsenal uye vakahwina kuti vaise divi ravo 10 kumusoro, kunyangwe Hull yakaenderera mberi ichirasikirwa ne32. Chester yakatamba ka28 muna 201415 sezvo Hull yaive nemushandirapamwe wakaoma uye yakadzoserwa kuChampionship, ichipedza mapoinzi matatu kubva pakachengeteka. 