VfL Wolfsburg reached the Champions League last 16 and dealt a knockout blow to Manchester United with a 3-2 victory on Tuesday that secured top spot in Group B and condemned their opponents to the Europa League.
United had taken an early lead in Germany when Anthony Martial expertly sidefooted home after 10 minutes, but Brazilian centre back Naldo drew the Germans level with a precise volley and Portuguese midfielder Vieirinha swept home to make it 2-1.
United were set to reach the next round when an own goal by Josuha Guilavogui levelled the scores at 2-2 with eight minutes left but Naldo grabbed his second and left the visitors needing PSV Eindhoven to lose at home to CSKA to reach the next round.
For a brief moment late in the second half it looked like United would get their wish, but PSV rallied to level and then snatch a 2-1 win that left them second in the standings on 10 points, two ahead of United and two behind Wolfsburg.
Manchester City 4
Shakhtar Donetsk 0
Real Madrid 8
CSKA Moscow 1
Atletico Madrid 2