Rangers had made heavy weather of overcoming First Division Ayr United in the last round and looked up against it here when they went a goal down after 23 minutes before Claudio Caniggia struck his sixth goal in four appearance at East End Park this season to bring the scores level.
Caniggia, Shota Arveladze and Ronald de Boer were all profligate in front of goal during a second-half onslaught but Rangers were unable to kill off the Fife side at the first time of asking
De Boer had been the main difference between the sides when Ayr were eventually despatched last month and the Dutch striker certainly looked in the mood again to similarly torment Dunfermline.
With Michael Mols and Peter Lovenkrands both out injured and Steven Thompson and Shota Arveladze on the bench, the onus fell on de Boer to hold the ball up and he performed the task superbly, linking up well with Caniggia and Neil McCann on the flanks.
Caniggia was enjoying some freedom down the right wing and created Rangers’ first real chance of the game when his in-swinging cross was just to high for de Boer and McCann – unsighted – was unable to direct his header on target.
Dunfermline’s last win over Rangers had came at home in the same competition 15 years ago and they boosted their chances of a shock repeat when they took the lead with 23 minutes gone, albeit in controversial circumstances.
Craig Brewster appeared to be at least two yards offside when he collected a pass just outside the Rangers penalty box but play was allowed to go on.
The veteran striker laid the ball off to David Grondin and he beat Stefan Klos with a well-struck low drive.
It had been harsh luck on a Rangers side that had dominated proceedings up until that point but the travelling support had only eight minutes to wait until they had a goal of their own to cheer.
Bert Konterman – making his first start of 2003 – found de Boer who pirouetted brilliantly to escape the attentions of Gus Macpherson.
A cute reverse pass let in Caniggia and the Argentine striker rolled the ball under Derek Stillie for the equaliser.
Play raced from end to end and after Stevy Crawford had blasted a shot just wide of Klos’ goal only the brilliance of Stillie twice denied Rangers a half-time lead.
The former Aberdeen goalkeeper tipped de Boer’s powerful header around the post for a corner and then made a great block to keep out a thunderous effort from Kevin Muscat.
It was not all one-way traffic, however, and Klos earned his corn with a brave block at the feet of Crawford in the last move of the first half.
The second half was even more incident-packed as both sides looked to book a semi-final place at the first attempt.
Both Caniggia and de Boer headed wide from dangerous McCann crosses before Stillie pulled off another great save to deny Ferguson’s well-placed shot.
The last 20 minutes seemed to fly past in a blur and Caniggia missed a golden chance when he was unable to turn his header goalwards from another great centre from McCann.
Rangers spent the last 10 minutes constantly attacking the Dunfermline goal and substitute Arveladze was unable to direct his header on target after Konterman had knocked on Arteta’s corner.
The match ended in a spectacular climax, with Rangers seemingly denied a penalty after Ged Brannan had tripped Arteta in the box.
With time ticking away, Ferguson was ordered off for a kick at Hunt as the Irishman juggled the ball on the touchline.
It was frantic stuff and both sides will need to go through it all again in next month’s replay.
Dunfermline: Stillie, McPherson, Wilson, McGarty, Grondin (Kilgannon 74), Nicholson (Hunt 52), Mason, Brannan, McGroarty, Crawford, Brewster
Subs not used: Ruitenbeek, Dair, Walker
Booked: Hunt (57), Brannan (90)
Rangers: Klos, Ricksen, Malcolm, Moore, Muscat, Konterman, Ferguson, Arteta, McCann (Arveladze 74), de Boer, Caniggia
Subs not used: McGregor, Ross, Thompson, Eggen
Booked: Ricksen (53), Muscat (57), Malcolm (81), Moore (85)
Sent off: Ferguson (89)
Referee: John Underhill
Man of the Match: Ronald de Boer