 St Ledger started 2009–10 as impressively as he had done the previous season but after only seven appearances for Preston, St Ledger joined Middlesbrough on loan with a view to a £4 million permanent move come the January transfer window.Rumours at the time told of how club chairman Derek Shaw informed St Ledger on the Preston team coach travelling to that evening's fixture at Scunthorpe that he had to join 'Boro as cash-strapped Preston needed the transfer money.St Ledger left his teammates en route to Lincolnshire and headed for Teesside.