An astonishing evening of fraught entertainment at Hampden Park saw Hibernian book their place in the CIS Insurance Cup final with a penalty shoot-out victory over holders Rangers.

In the end, the Old Firm's six-year domination of the domestic trophies was ended when Frank de Boer - a famous misser of penalties for Holland - trundled a spot-kick against a post to add to his personal woe and that of his new employers in one stroke.

Bobby Williamson's youthful Hibs side, who famously came from behind to beat Celtic in the previous round, staged a remarkable comeback to set up a deserved final with Livingston.

That it should have been decided on penalties was appropriate because Hibs goalkeeper Daniel Andersson, who pulled off a breath-taking shoot-out save to deny Zura Khizanishvili, had made done likewise to keep out Mikel Arteta in the first half of normal time.

Andersson conceded that penalty himself by bringing down Ronald de Boer.

He was helpless when Michael Mols, who had blasted over an inviting chance in front of goal in only the second minute, slotted home a Maurice Ross pass following a quick free-kick move in the 40th minute.

As the minutes ticked away in the second period, Hibernian appeared to have been typecast in the role of plucky losers until Williamson made a tactical masterstroke with fewer than 15 minutes remaining.

He sent on striker Stephen Dobbie, the youngster Rangers had discarded in the summer, in what proved to be an inspired move.

Dobbie combined with man-of-the-match Derek Riordan and then blasted an equaliser past Rangers goalkeeper Stefan Klos, who had previously had hardly a shot to save.

The goal transformed the tie as Rangers, with seven over-thirties on the pitch following a trio of substitutions, found themselves swamped by waves of attacks instigated by more youthful legs.

The holders were extremely fortunate to find themselves still in the tie before the end of the 90 minutes, because Ross appeared to have barged over Garry O'Connor in the box.

But referee Kenny Clark, who had had no hesitation penalising Andersson for the earlier penalty and was constantly waving his yellow card at offenders, kept his whistle away from his mouth on this occasion.

Television cameras picked up what appeared to be an elbow in Riordan's face by Fernando Ricksen - and that could prove to be further trouble for Alex McLeish's side, who now have only the Tennents Scottish Cup as a realistic silverware target.

Dobbie was to prove his side's saviour in extra-time as well, because he was perfectly placed on his own goalline to block a shot from Craig Moore which had evaded Andersson.

Substitute Egil Ostenstad was inches away from poking a Paolo Vanoli cross into the net with virtually the last kick of extra time.

Dobbie went on to join a jaw-dropping number of penalty shoot-out failures - but it was Frank de Boer whose miss was to prove decisive.

Teams

Hibernian Andersson, Caldwell, Doumbe, Murdock, Edge (Dobbie 76), Scott Brown, Wiss (Whittaker 57), Reid (McManus 45), Thomson, O'Connor, Riordan.

Subs Not Used: Nicol, Alistair Brown.

Booked: Caldwell, O'Connor, McManus, Thomson.

Goals: Dobbie 79.

Rangers Klos, Ross (Vanoli 88), Frank de Boer, Moore, Ball, Arteta (Khizanishvili 73), Ricksen, Nerlinger, Mols, Ronald de Boer (Ostenstad 73), Arveladze.

Subs Not Used: Capucho, McGregor.

Booked: Ross, Ostenstad, Vanoli.

Goals: Mols 40.

Att: 27,954

Ref: K Clark (Scotland).