Manchester United draw in Spain in Europa League last 16 as Spurs beaten

Manchester United drew 1-1 away to Real Sociedad in the first leg of their Europa League last-16 tie on Thursday, while Tottenham suffered a 1-0 loss at Dutch side AZ Alkmaar.

Joshua Zirkzee drilled in from just outside the area to give United the lead on 57 minutes in San Sebastian but Mikel Oyarzabal levelled from the spot after Bruno Fernandes was punished for a handball.

Zirkzee cut a distraught figure after missing the decisive penalty in last week's FA Cup shootout loss to Fulham and has endured a testing first season at United, whose only remaining hope of silverware is in the Europa League. He scored for the first time in Europe this term, unleashing a sharp low drive from 20 yards after being teed up by Alejandro Garnacho's inviting pass.

But Ruben Amorim's side could not hold on to their advantage as Fernandes handled at a corner, with Oyarzabal confidently converting his spot-kick.

Elsewhere, Lucas Bergvall's first-half own goal condemned Spurs to defeat in the Netherlands. Rangers recorded an impressive 3-1 win away to Jose Mourinho's Fenerbahce. Lyon also took a big stride towards the quarterfinals with a 3-1 victory at Romanians FCSB.