Roberto Soldado's embarrassing mistake paved the way for Tottenham's Europa League exit against Fiorentina.
The trip to Florence was always going to be a tough ask for Mauricio Pochettino's side, given the last-32 tie was poised at 1-1 and their Capital One Cup final against Chelsea loomed large.
The Spurs head coach insisted beforehand that Sunday would not be a distraction and that this was merely their "first final" - one in which they paid for a lack of cutting edge, with second-half efforts from Mario Gomez and Mohamed Salah securing Fiorentina a 2-0 victory. Things could have so different had Christian Eriksen been awarded an early penalty or, more importantly, Soldado not produced another clip for his growing reel of gaffes.
Clearly bereft of confidence, the misfiring striker decided to pass out to Nacer Chadli when through one-on-one, only for the under-hit ball to be easily gathered by Fiorentina goalkeeper Neto.
It was a shocking error that Pochettino's men would pay for on a night in which their bright start at the Stadio Artemio Franchi would peter out.
After handball appeals against Federico Fazio and a wasted chance by Milan Badelj, both were involved as the latter read the former's poor pass and played through Gomez to fire home.
It was not long until Spurs, who saw goalkeeping coach Toni Jimenez sent off, were punished once again as Jan Vertonghen was dispossessed by Salah and the Chelsea loanee lashed home.
Substitute Harry Kane did find the net, only for offside to be called on a night which was is far from ideal preparation for Sunday's trip to Wembley.