Two-time holders Inter Milan were knocked out of the Italian Cup last 16 on Wednesday after a last-gasp 2-1 loss to Bologna.
Defender Sam Beukema and attacker Dan Ndoye scored in the second half of extra time at the San Siro to set up a quarterfinal tie with Fiorentina after Carlos Augusto had opened the scoring for the Serie A leaders.
Bologna, managed by ex-Inter midfielder Thiago Motta, join Fiorentina, Lazio and Frosinone, who beat league champions Napoli 4-0 on Tuesday, in the last eight.
The remaining four last-16 ties will be held early next month with the only Serie B side left in the competition Cremonese heading to Roma on January 3.
Inter coach Simone Inzaghi made plenty of changes for the game during a busy festive period, keeping the likes of playmaker Hakan Calhanoglu as well as in-form attacker Marcus Thuram out of the starting 11.
Despite Inter's first-half dominance, Bologna, fourth in Serie A, came closest to opening the scoring as Giovanni Fabbian tested Inter's Emil Audero in the goal with a volley in the 13th minute.
The best of Inter's nine first-half shots on goal fell to Davide Frattesi but Federico Ravaglia parried the shot wide after half an hour.
Inter thought they had the breakthrough with 25 minutes to play but Serie A's top scorer Lautaro Martinez had his penalty saved by Ravaglia after Bologna's teenage defender Tommaso Corazza was penalised for handball.
Martinez came close to opening the scoring again three minutes later but his effort skimmed over the crossbar after a smart dummy outside the box.
With 16 minutes to play Inzaghi brought Thuram onto the field, looking for the France attacker's third goal in four games.
Bologna showed why they had lost just twice this season, conceding just 12 times in 16 matches, with some impressive last-gasp defending and a few impressive saves from Ravaglia in just his third appearance of the season, late on in normal time.
The long-awaited Inter breakthrough came after 145 seconds of the first half of extra time as Augusto headed home from Federico Dimarco's corner for Inter.
With 112 minutes gone, Motta's outfit drew level with Beukema's side-footed effort, superbly assisted by fellow Dutchman Joshua Zirkzee, who ended up off the field in his attempts to keep the ball in play.
Bologna's surprise victory was secured with five minutes of extra time remaining as Zirkzee provided a second assist, setting up Switzerland winger Ndoye for the winner on the counter-attack.
Inter's next game is Saturday's home match against Lecce after Bologna host Atalanta earlier in the day.