Leeds' dream of European glory this season could be over before it has even started as one of the favourites to lift the UEFA Cup were embarrassingly beaten by Portuguese minnows Maritimo.
David O'Leary's side looked as if they were on vacation on the holiday island of Madeira as they suffered a shock 1-0 loss in the first leg of their first-round tie at the Estadio dos Barreiros.
Bruno Fernandes' soft 34th-minute free-kick was all that separated the sides, but the scoreline could have been far worse, and such was Leeds' frustration that at one point Dominic Matteo and Jason Wilcox were seen arguing among themselves.
This was a match which should have represented a watershed in O'Leary's career for it was at the same venue and at the same stage of the competition exactly three years ago that one United era came to an end and another began.
A penalty shootout victory over Maritimo proved to be George Graham's last match in charge, with O'Leary then handed the reins upon the club's return to Leeds/Bradford Airport.
Leeds looked as if their heads were still in the clouds in the wake of the Champions League euphoria which swept over them before their eventual exit to runners-up Valencia.
The tidy, compact ground - overlooking the Atlantic Ocean - was also a far cry from the overwhelming delights of the Nou Camp, Bernabeu, San Siro and the Olympic Stadiums in Rome and Munich.
In such glorious venues Leeds rose to the challenge of their surroundings and the opposition which they faced, but on this occasion it was a case of being brought back down to earth - and with an almighty thump.
This was one of their worst performances since O'Leary took charge.
Leeds were slow and sluggish and at times almost looked disinterested as Maritimo created a number of clear chances, and but for Nigel Martyn making two fine saves notably from Dinda and Quim Ferraz - then the deficit going into next Thursday's second leg could have been far worse.
The breakthrough came after Rio Ferdinand had fouled Quim, resulting in Bruno lofting a hopeful free-kick into the area where Matteo failed to clear while under challenge from the tall centre-back Mitchell van der Gaag.
It left Martyn unsighted, and despite a late, despairing dive, the ball drifted inside his left-hand post to the stunned amazement of all in the Leeds camp.
At times O'Leary was out of his dugout barking instructions, but he sat down for the final half hour and looked on in bewilderment. "I'm disappointed," he said later. "Thank God it's not three points that we have dropped in the Champions League.
"It's the UEFA Cup and as the saying goes, it's only half-time, so it's not over yet. We are missing vital players in vital positions. But it is not a matter of complacency. We are a better team. The time to be judged will be after both games are over.
"But I hope this serves as a kick up the backside, and if it doesn't then we are going to be out of this tournament."
MARITIMO: Nelson, Albertino, Sergio, Zeca, Dinda (Santos 85), Andre. (Alan 75), Fernandes Bruno, Quim (Gaucho 61), Briguel, Kenedy., van der Gaag.
LEEDS: Martyn, Kelly, Matteo, Ferdinand, Harte, Mills, Batty, McPhail (Wilcox 57), Kewell, Keane, Viduka. Booked: McPhail, Kelly.
Referee: J Van Hulten (Holland).