Season 2005–06 was a season of missed opportunities for Hibernian. The team started strongly in the league, winning 10 of their first 14 games, but this form dipped after Christmas. The Scottish Cup seemed to be opening up for Hibs after they defeated Rangers 3–0 at Ibrox in the fourth round, but they then lost 4–0 in an Edinburgh derby semi–final against Hearts. Hibs lost 3–0 in the quarter–final of the Scottish League Cup at Dunfermline, and were well beaten by Dnipro Dnipropetrovsk in the UEFA Cup.

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. This was followed by a series of friendly matches against Scottish Football League clubs. Unusually, two of these matches were played on the same day as Hibs split their squad between matches at Ayr United and Queen of the South. 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.

Hibs began the season inauspiciously, drawing 1–1 at home to Dunfermline, although a draw represented something of a recovery having been a goal and a man down at half time. 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. Hibs lost 4–0 as Hearts went on to start the season with eight consecutive league wins.

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