2008–09 Heart of Midlothian F.C. season

[1] The club began the season with a home win against Motherwell and had a good run in the early stages of the campaign, climbing as high as second in the table in late September.

[4] Hearts entered the Scottish League Cup at the second round and were given a tough game by First Division side Airdrie United, being defeated on penalties after a 0–0 draw.

The club entered the Scottish Cup in the Fourth Round where they faced Edinburgh derby rivals Hibernian at Easter Road.

Hearts won the game 2–0 with goals from Christian Nadé and Gary Glen to set up a Fifth Round tie with Falkirk.

On 28 February Hearts beat fellow 3rd place hopefuls, Dundee Utd 1–0 at Tannadice with Michael Stewart's second half strike.

This moved them 5 points clear in 3rd place, following which Hearts then defeated Motherwell 2–1 at Tynecastle with a last minute goal from Ruben Palazuelos.

During the January transfer window the club lost Christophe Berra to Wolverhampton Wanderers in a deal worth around £2.5 million.