On 13 August 2009, Hearts manager Csaba Laszlo announced the appointment of midfielder Michael Stewart to the role of club captain, replacing Robbie Neilson after his move to Leicester City.
Despite a poor start to the season Hearts recorded a 1–0 win over Celtic in the League Cup at Parkhead with a Michael Stewart penalty.
He did not enjoy a successful start as Hearts crashed out of the League Cup, losing 1–0 to St Mirren, with Billy Mehmet the only scorer.
[6] Heart of Midlothian made five signings over the summer break: Ian Black, Dawid Kucharski, Ismaël Bouzid, Suso Santana and David Witteveen.
Before the January transfer window was closed, Jim Jefferies signed Ryan Stevenson from Ayr United for a five figure undisclosed fee.