FC Copenhagen 2 – Manchester City 2 (UEFA Cup, February 19, 2009) A real howler from home keeper Jesper Christiansen saw City take the lead as he let a tame shot from Nedum Onuoha slip through his hands. Aliton Almeida equalised with a firm header unmarked from a corner. Five minutes later Stephen Ireland put City ahead again from an SWP cross. But at the death the porous City defence was exposed once more, Ndoye picked out an unmarked Martin Vingaard who equalised with an injury time header.
Shakhtar Donetsk 2 – Tottenham 0 (UEFA Cup, February 19, 2009) Just a minute after coming on, Yevgen Seleznov headed Shakhtar Donetsk in front from a Jadson free kick. Jadson claimed the second late on to put the Ukranian side in the driving seat ahead of the second leg in London.
Marseille 0 – FC Twente 1 (UEFA Cup, February 19, 2009) Marko Arnautovic tapped Twente into the lead at Marseille.
Lech Poznan 2 – Udinese 2 (UEFA Cup, February 19, 2009) Early in the second half the Italians took a two goal lead through a fine header from Fabio Quagliarella and an og by Manuel Abeloda. Lech Poznan kept the tie alive with two goals in the final ten minutes, the first a tap-in for Hernan Rengifo and the second redemption for Manuel Abeloda with a header at the back post.
Fiorentina 0 – Ajax 1 (UEFA Cup, February 19, 2009) Adrian Mutu had a goal chalked out for offside after only six minutes. Ajax took the lead on the hour mark when Urby Emanuelson fed Kennedy Bakircioglu on the edge of the box and he crashed home a shot off the underside of the bar.