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Real Madrid fell seven points behind La Liga leaders Barcelona after Vedat Muriqi's late winner for Mallorca inflicted a major title blow on Alvaro Arbeloa's side.
While Mallorca celebrated moving two points clear of the relegation zone with their afternoon victory, Real's gloom deepened further on Saturday evening.
Already four points adrift of Barcelona, that became seven when Hansi Flick's side came from behind to beat Atletico Madrid in the late game.
Eight rounds of games remain, with Barcelona firmly in the driving seat to retain their title.
Hosts Mallorca went ahead against Real four minutes before half-time when Manu Morlanes met a cross from the right delivered by Pablo Maffeo, took a touch to compose himself, and slotted into the bottom right corner.
Real thought they had salvaged a point in the 88th minute when Eder Militao headed in superbly from Trent Alexander-Arnold's corner.
However, Muriqi had other ideas and struck his 19th league goal of the season in the first minute of stoppage time to give the hosts a superb win.
Arbeloa's visitors had several chances before Mallorca took the lead, but home goalkeeper Leo Roman was in fine form.
Kylian Mbappe raced past two Mallorca defenders and swung a shot towards goal but Roman's outstretched leg denied him.
The France captain was thwarted once more when Roman pushed his curled effort behind when it was headed into the far corner.
Arda Guler's low driven shot was well saved by Roman as Los Blancos continued to be frustrated.
At the other end, Morlanes headed over from six yards but made up for his miss by putting Mallorca ahead.
The late drama left the visitors dejected, with a first defeat by Mallorca since February 2023 proving a major blow to Real's prospects of La Liga glory.
Real will hope to return to winning ways when they host Bayern Munich in the first leg of their Champions League quarter-final on Tuesday (20:00 BST).
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