Tottenham, Birmingham and Celtic all crashed out of the Europa League, despite none of them losing.
Spurs thrashed Irish side Shamrock Rovers 4-0, with goals from Steven Pienaar, Andros Townsend, Jermain Defoe and Harry Kane.
But its wasn't enough to take Harry Redknapp's men through, as they ended up finishing third in their group.
Elsewhere Birmingham beat Slovenian league leaders NK Maribor 1-0 and Celtic drew 1-1 with Udinese in Italy.
Those results mean that it is only Stoke City who will join the two Manchester clubs in the knockout stages of the competition.