Juventus endured a disheartening 4-1 loss against lowly Empoli in Serie A on Monday, exacerbated by a 10-point penalty imposed due to their transfer dealings, considerably diminishing their chances of qualifying for the prestigious Champions League.
Two goals by Francesco Caputo and a strike from Sebastiano Luperto made it 3-0 for Empoli just after halftime before Federico Chiesa pulled a goal back for Juve five minutes from time and Roberto Piccoli sealed Empoli's win in stoppage time.
Juve, who learned about the new verdict shortly before kickoff, dropped from second to seventh following the points deduction.
They are on 59 points, one behind AS Roma, who occupy the final European qualifying place in sixth and five adrift of fourth-placed AC Milan with two games left.
"Summing up a season in an evening like this is an understatement," said Juve coach Massimiliano Allegri. "It was a strange situation; the sentence came out 10 minutes before the match.
"Juventus are used to winning; we have to close ranks. There are six points up for grabs and Milan arrive on Sunday."
Arkadiusz Milik hit the crossbar following a corner in Juve's intense start to the game and Federico Gatti had a goal ruled out in a follow-up due to a foul in the buildup.
But things went downhill for Juventus as Empoli were awarded a penalty for Milik's foul on Nicolo Cambiaghi and striker Caputo converted from the spot to put the hosts in front in the 18th minute.
It was 2-0 three minutes later when defender Luperto doubled Empoli's lead following a corner as he struck into the roof of the net on a rebound.
While first-half chances from Dusan Vlahovic and Gleison Bremer did not cut the deficit for Juve, Empoli continued to show incredible determination after the break and added another goal two minutes into the second period.
Midfielder Jean-Daniel Akpa Akpro went on a solo run and squared the ball to Caputo, who made it 3-0 with a chipped finish.
Juventus ended their failings in front of the goal when halftime substitute Chiesa pulled a goal back with a low strike five minutes from time in his 200th appearance in Serie A.
But it was too little too late for powerless Juventus, who conceded again in stoppage time when forward Piccoli moved quickly past three Juve defenders to seal the win.
Juventus, knocked out in the Europa League semifinals on Thursday by Sevilla following a 3-2 aggregate loss, previously won all five away matches against Empoli under Allegri.