 Mark Wright has managed him at the four clubs he has been in charge of, namely Southport, Oxford, Chester and Peterborough.Bolland had earlier played in non-league football for clubs including Altrincham, Salford City, Trafford and Knowsley United.Bolland struggled to stake a place in the first-team side at Chester under new manager Bobby Williamson in 2007–08, making just three appearances.