Julio Dely Valdes scored twice to earn Malaga a hard-fought victory at Elland Road and eliminate Leeds from the Uefa Cup.
Despite the loss of an early goal and striker Michael Bridges with a serious injury, Leeds replied through Eirik Bakke and pushed hard for a winner before Dely Valdes' late second goal settled the contest.
The tone of the match had been set after 16 minutes, when Lee Bowyer stamped on Gerardo to ensure a full-blooded physical encounter followed.
Key moments
Occasional moments of skill and flair were interspersed with crunching tackles and off-the-ball incidents on a bitter night at Elland Road.
The defeat adds to the problems facing Leeds manager Terry Venables, whose team are now out of Europe and facing a domestic relegation battle.
Malaga settled quickly and scored after just eight minutes.
Kiki Musampa got the better of Danny Mills on the right-hand side and cut the ball back for Dely Valdes to slip the ball home.
Leeds had already lost Bridges with a ruptured Achilles tendon and the goal only added to the team's considerable problems.
Bowyer then lit the blue touch paper with an X-rated tackle on Gerardo, which he followed with a vicious stamp on the player's head.
The Leeds midfielder was fortunate to only receive a booking.
Bakke equalised for the home team with a cushioned volley from a tight angle after an intelligent knock-back across goal from Robbie Fowler.
"
I felt we were so much better for long periods of time
"
Terry Venables
The Norwegian's reward for scoring was a boot in the nether regions from a Malaga player shortly afterwards.
Dely Valdes headed narrowly over and almost pounced on a half-save from Paul Robinson, while Marcelo Romero forced an excellent save with a brilliant long-range shot after the Spanish team tried to add to their advantage.
Bowyer almost scored with a flying header early in the second-half but clear-cut chances were at a premium as Malaga concentrated on preserving their slender advantage.
A series of niggling challenges disrupted the flow of the game, but Leeds almost profited from a needless foul when Michael Duberry rose to the subsequent free-kick, but his effort narrowly missed.
Minutes later Robinson got down quickly to deny Musampa's superbly struck snapshot.
But Dely Valdes made the most of a fortunate ricochet to smash the ball past Robinson with 10 minutes remaining and take the tie beyond Leeds.
And Robinson was required to make a good save with full-time looming to prevent Dario Silva from increasing Malaga's lead.
Leeds: Robinson, Mills, Woodgate, Duberry, Kelly, Bowyer,
Bakke, Okon, Wilcox, Smith, Bridges (Fowler 9).
Subs Not Used: Martyn, Harte, Radebe, McPhail, Seth Johnson,
Kilgallon.
Booked: Bowyer, Smith.
Malaga: Contreras, Josemi, Fernando Sanz, Roteta, Valcarce,
Manu (Sandro 57), Gerardo, Romero, Musampa (Miguel Angel 78),
Silva, Dely Valdes (Litos 90).
Subs Not Used: Arnau, Iznata, Leko, Koke.
Booked: Gerardo, Valcarce, Silva, Fernando Sanz, Sandro.
Attendance: 34,123
Referee: Massimo Busacca (Switzerland).