Dunfermline Athletic 3 (Hamilton 16, Simmons 28, McGuire 47) Rangers 2 (Boyd 2 [54, 68])
Attendance 7,231
The defeat leaves the new Rangers' Manager, whoever he may be, with effectively only the UEFA Cup to compete for during the remainder of the season.
Acting Manager Ian Durrant selected the first Rangers team of the post-Paul Le Guen Era, making three changes from Motherwell with Barry Ferguson, who has stabbed the last two Ibrox Managers in the back, and who is not fit to lace the boots of many of the great Light Blue captains of the past, shamefully returning to the starting line-up (although thankfully not as captain). Julien Rodriguez and Nacho Novo also played from the start - with the absentees being the injured Jeremy Clement, Chris Burke and the suspended Dado Prso.
The Ibrox line-up included just one Paul Le Guen signing - Karl Svensson.
The Light Blue legions, out in massive numbers, gave a warm welcome to Ian Durrant before kick-off, but there was a pathetic turn-out of Pars' fans, with perhaps as few as 300 in the Norrie McCathie Stand.
Rangers opened positively, but the first shot on target in eleven minutes saw Stephen Simmons test Allan McGregor with a snap-shot from 25 yards that the goalkeeper parried.
Sixty seconds later Svensson's header from a Ferguson cross was held by home goalkeeper Roddy McKenzie.
Rangers were hungry for the opener - and there was a moment of controversy on the quarter-hour mark when Alan Hutton's header from a Charlie Adam cross was blocked on the line by Scott Morrison. There were loud claims for a penalty on the grounds of handball, but for once Referee Iain Brines got a decision right, the ball appearing to strike the defender on the shoulder.
Unbelievably the opening goal when it arrived sixty seconds later came at the other end - Jim Hamilton netting after an Owen Morrison cross was completely missed by Kris Boyd, another Ranger whom many felt should never wear the Light Blue again, given his role in the undermining of Paul Le Guen and his deliberate lack of effort in the League Cup defeat by St. Johnstone.
The visitors' defence was a complete and utter shambles, illustrated in 26 minutes when Hamilton's free header from an Owen Morrison corner was blocked by McGregor.
Two minutes later it was 2-0 with Simmons netting at the second attempt after Owen Morrison's overhead-kick had caused total confusion in the visitors' defence - the ball bouncing around like a pinball.
Rangers were now in deep trouble - and five minutes later Ian Durrant introduced Chris Burke in place of Rodriguez, with Brahim Hemdani dropping back from midfield into central defence. Thus the interim boss had reversed his first team selection decision.
The score remained unchanged until the interval, with Dunfermline as likely to increase their lead as to see it reduced.
The Ibrox men were in desperate need of an early goal to get back into the game, yet unbelievably within two minutes of the restart it was 3-0 when Phil McGuire headed home an Owen Morrison corner - with once again the centre of defence badly at fault.
This was humiliation against a side who had not scored in their previous five games - and even though Burke tested McKenzie with an angled drive in 52 minutes within sixty seconds it was almost four when Svensson's error presented Hamilton with a clear sight of goal only for the centre to shoot straight at McGregor.
Rangers at last got their act together and reduced the deficit in 54 minutes when a flowing Ferguson - Gavin Rae move down the right saw Boyd rifle the cutback home.
The Pars were still threatening to add to their score however - Steve Crawford cutting inside on the hour only to see McGregor hold his eighteen-yard shot.
Three minutes later Boyd had the ball in the net again with a header from Hutton's cross only for the goal to be disallowed for a foul.
Thomas Buffel replaced Adam in 64 minutes - and four minutes later it was 3-2 when Boyd headed home Ian Murray's cross.
Suddenly it was an entirely different ball-game, and Rangers piled on the pressure with Ferguson's header from Burke's cross striking the crossbar three minutes later.
Boyd almost completed his hat-trick in 73 minutes when he shot inches wide from a Burke pass, then sixty seconds later another Burke opening released Ferguson who shot straight at McKenzie.
For all their pressure however time ran out on Rangers and the final whistle signalled a second Scottish Cup elimination at the first time of asking in three years. Indeed since last winning the national tournament in 2003 the Ibrox men have failed to reach even the semi-finals.
Afterwards a bitterly disappointed Ian Durrant was scathingly critical of his charges:
“Poor defending cost us the game, as it has cost us all season. Shocking defending - I asked the players to go in where it hurt, but that kind of player's a dying breed. We started nervously, and gave the ball away too easily. Jim Hamilton terrorised our back four. Players have got to stand up and be counted. This is a massive job even when winning. There are talented players in the squad. We should have scored four or five times in the second half. I wanted a response from the first minute - you can't just switch it on or off when it suits you, or just roll your sleeves up for the last half-hour.”
Dunermline Manager Stephen Kenny added perhaps the most telling comment of the day:
“We played better against Motherwell” (Boxing Day, lost 0-2)
DUNFERMLINE ATHLETIC McKenzie; Ross, McGuire, Wilson, S. Morrison; Simmons, O'Brien, Darren Young, O. Morrison; Hamilton, Crawford UNUSED SUBS Murdoch, Tod, Woods, Bamba, Daquin
RANGERS McGregor; Hutton, Rodriguez, Svensson, Murray; Rae, Ferguson, Hemdani, Adam; Novo, Boyd UNUSED SUBS Gallacher, Lennon, Buffel, Burke, Papac
REFEREE Iain Brines