Manchester United suffered more misery as Danish champions FC Midtjylland fought back from a goal down to win the first leg of their Europa League last-32 tie 2-1.
United were seeking to win back some pride in Europe after crashing out of the Champions League before Christmas.
But manager Louis van Gaal's domestic problems were transferred to the continent once again as his injury-hit United side suffered against opponents who had not played for two months because of Denmark's winter break.
Van Gaal lost goalkeeper David De Gea to injury in the pre-match warm-up, but there was some good news when Memphis Depay's close-range finish put United in front after 37 minutes.
But Pione Sisto - capitalising on a Michael Carrick error - equalised seven minutes later, and a fine strike from substitute Paul Onuachu with 13 minutes to go handed Midtjylland a deserved victory set to be celebrated long into the Danish night.
Tottenham and Fiorentina will meet at White Hart Lane next week with the tie nicely poised at 1-1.
Nacer Chadli put Spurs ahead with a dubious penalty 37th-minute penalty after Ben Davies went down in the box following minimal contact from Nenad Tomovic.
But Federico Bernardeschi's deflected second-half effort raised Fiorentina hopes that they can repeat their Europa League success over Spurs 12 months ago.
Reigning Europa League champions Sevilla thrashed Molde 3-0 to almost certainly book their place in the last 16.
Fernando Llorente struck twice and Kevin Gameiro added a third as Ole Gunnar Solskjaer's men were blown away.
Fellow Spaniards Villarreal will also defend a first-leg leg after beating Napoli 1-0 at El Madrigal.
Denis Suarez - who helped Sevilla win the Europa League last season - came up with the decisive moment when his dipping free-kick beat goalkeeper Jose Rein via the underside of the crossbar.
Goals from Lukasz Piszczek and Marco Reus handed Borussia Dortmund a 2-0 win over Porto.
Piszczek put Dortmund on the way to a comfortable victory after just six minutes at Signal Iduna Park and Reus made the result certain 19 minutes from time to leave Porto with an uphill task in Portugal next week.
St Etienne beat Basle 3-2 in an entertaining contest at the Stade Geoffroy-Guichard, with substitute Jean-Christophe Bahebeck the hero.
Moustapha Sall and Kevin Monnet-Paquet scored to put Les Verts in cruise control, but Basle were level by the hour mark through Walter Samuel and a Marc Janko penalty.
But Bahebeck had the final word after 77 minutes to give St Etienne a narrow lead to take to Switzerland next week.
Anderlecht beat Olympiacos 1-0 at home with Kara Mbodji's controversial 67th-minute effort proving the difference.
The goal was only allowed after a lengthy discussion between referee and linesman, much to the Greeks' displeasure who had complained of a foul on goalkeeper Roberto.