 On 25 August, Chester started for West Brom in a League Cup match against Port Vale, both sides failed to score and the game went to penalties, Chester scored the decisive penalty enabling West Brom to progress to the next round of the competition.West Brom manager Tony Pulis played Chester in an unfamiliar right-back role instead of centre back leading to Chester becoming unhappy at the Hawthorns.In August 2016 West Brom accepted a bid for Chester from Aston Villa.