2005–06 Hibernian F.C. season

Hibs went on a three match tour of Ireland in early July, beating St Patrick's Athletic and drawing with Cork City and Shamrock Rovers.

Hibs then played a match against Rot-Weiss Essen to mark the 50th anniversary of the first European Cup competition before completing their pre-season schedule with a 1–0 win against Hartlepool United.

The second match was an Edinburgh derby at Tynecastle, where Hibs felt the full brunt of a powerful new Hearts side under the management of George Burley.

Ivan Sproule, who had been thinking of returning to his native Northern Ireland,[2] scored all the goals as a second-half substitute for Garry O'Connor.

[6] Having finished third in the Scottish Premier League table in the previous season, Hibs qualified directly into the first round proper of the UEFA Cup.

Their preparations for the game were not helped when Rangers made an offer to sign Derek Riordan, Hibs' top scorer, in the week before the match.

Riordan ended up making a cameo appearance, setting up the third goal for Chris Killen in a second 3–0 win for Hibs at Ibrox, and their third victory in all over Rangers that season.

Gretna beat Dundee 3–0 in the first semi-final, leaving Hibs and Hearts to contest the right to face a Second Division side in a Cup Final where they would be heavy favourite.

Captain Ian Murray moved to Rangers under freedom of contract, while Hibs signed Michael Stewart, who had been on loan at Hearts.

Tony Mowbray also signed Zbigniew Małkowski to play in goal, as Simon Brown had made some errors towards the end of the previous season.

During the winter, Hibs brought in Chris Killen, Oumar Kondé and Paul Dalglish in an attempt to strengthen a squad that was being stretched by injuries.

[11] O'Connor's transfer started a trend of Hibs selling players, as Kevin Thomson, Scott Brown, Steven Whittaker and David Murphy all moved for fees in excess of £1.5M over the course of the next two years.