Gennaro Gattuso suffered defeat in his first Europa League game in charge as AC Milan rounded out an otherwise successful Group D campaign with a 2-0 loss away to Rijecka.
The Rossoneri's unbeaten record in Europe this season came to a disappointing end in Croatia, leaving their new manager still waiting for his first victory since taking over from Vincenzo Montella.
Denied at the death by Benevento goalkeeper Alberto Brignoli's unlikely equaliser on Sunday, Gattuso saw a much-changed XI out-fought and out-thought by a side with nothing to play for but pride.
Jakov Puljic's sumptuous free-kick beyond stand-in goalkeeper Marco Storari gave Rijecka the lead after just seven minutes.
Mario Gavranovic's first-time finish from a left-wing cross confirmed a famous win for the hosts, meaning Milan have now triumphed in just four of their last 15 outings in all competitions
Full-time— AC Milan (@acmilan) December 7, 2017
Not the best of nights for us but we'll be back for the Round of Last 16 in February!
Non una serata da ricordare ma saremo di nuovo in #UEL a febbraio per i sedicesimi#RIJACM #ForzaMilan pic.twitter.com/b1gA6fJfH2
While already certain of qualifying for the knockout stages as group winners, Gattuso had called for his players to show "desire" in his pre-match press conference, aware of the need to arrest a worrying run of form.
Yet his inspiring words appeared to fall on deaf ears judging by his side's first-half display, even when taking into consideration the absence of several first-team regulars.
Sluggish from the outset, they fell behind in the seventh minute when Lucas Biglia's foul just outside the area allowed Puljic to curl a free-kick over the wall and beyond Marco Storari's desperate dive.
The scorer missed an excellent chance to heap further misery on the visitors before the break too, heading a teasing cross from the right narrowly wide of the target.
Milan created little yet still could easily have drawn level before half-time, with Andre Silva's lob clearing goalkeeper Simon Sluga but ending up sitting on the roof of the net, rather than in the back of it.
Rijecka moved further clear just two minutes into the second half, Gavranovic's rather scruffy finish from Zoran Kvrzic's low delivery doubling their advantage.
Conceding for a second time seemed to briefly bring Milan to life as an attacking force, with Luca Antonelli seeing an on-target effort blocked by a home defender.
Patrick Cutrone wasted their best chance to half the deficit though, the forward seeing a downward header loop over after he'd misjudged his jump to meet Davide Calabria's tantalising cross.
To round out a thoroughly miserable road trip for Gattuso, a late booking picked up by Manuel Locatelli means the midfielder will be suspended for the next game in Europe.
Key Opta stats:
- AC Milan lost a Europa League/UEFA Cup match for the first time since April 2002 (since then eight wins and six draws).
- Puljic’s goal (7’) was the fastest conceded by AC Milan in Europa League this season.
- AC Milan failed to fire a single shot on target for the first time in Europa League this season.
- Rijeka netted two goals with their only two shots on target.
|I want to fight the champion! - Joshua reiterates Wilder in April ambition|
|Gundogan glad to leave Christmas holidays behind|
|I know how it feels and it hurts - Gundogan on Sterling abuse|
|Celtic 1 Red Bull Salzburg 2: Scottish champions through despite defeat|
|Olympiacos 3 AC Milan 1: Rossoneri crash out of Europa League|
|Arsenal 1 Qarabag 0: Lacazette on target as Saka shines|
|Hansen to leave: All Blacks will take time to name replacement|
|Chelsea condemn alleged anti-Semitic chanting from fans|
|Hansen to leave: The best Opta facts from New Zealand coach´s tenure|
|Hansen to leave: Five contenders to be the next All Blacks coach|
|Hansen to leave: Highs and highs of his All Blacks reign|
|Hansen to leave All Blacks after World Cup|
|Rapid Vienna 1 Rangers 0: Late Ljubicic winner sends Gerrard´s men out|
|Beckham continues to miss Giants practice with quad injury|
|Vidi 2 Chelsea 2: Giroud spares Sarri´s side in lacklustre draw|
|Paris Saint-Germain and Marseille fixtures among latest Ligue 1 cancellations|
|Santos turn to ex-Argentina boss Sampaoli|
|Muller could miss Champions League last 16 after Tagliafico kick|
|Home hope Bekker out in front at Alfred Dunhill Championship|
|Van Bommel in touch with Robben over PSV reunion|
|Pinarello chief confident over Team Sky future|
|Stade make Ospreys tickets free in tribute to teenager|
|WRC great Loeb seals Hyundai switch|
|Madrid rumours better than sack talk, says Pochettino|
|Nadal to join Federer at 2019 Laver Cup|
|Prigoda smashes world record, Hosszu dethroned in Hangzhou|
|Former Juve CEO Marotta takes over at Inter|
|Glenn to stand down as FA boss next year|
|Muller apologises to Tagliafico for kick to the head|
|Pereira pleads for more Manchester United chances|
|Griffin hails ´phenomenal´ Lowry after Warriors demolition|
|I´ve played with Zidane and Henry, but Messi is something else – Pires|
|Dragons forward Jack de Belin charged with sexual assault|
|Durant: Raptors are the real deal|
|Cocu bids farewell to Fenerbahce after ´mutual agreement´ is made over October sacking|
|Australia unchanged for historic Perth Test|
|Champions League draw: The possible last-16 ties|
|Southee happy to be back on home soil|
|I wouldn´t swap Dembele for Neymar – Pires|
|Canelo ready to risk heavy weather against Fielding|
|Raptors upstage Warriors, Davis leads Pelicans with 44 points|
|India skipper Kohli excited by green Perth wicket|
|PSG? I haven´t decided my future yet – De Jong|
|Marcelo: Real Madrid don´t have attitude problem|
|India pair Ashwin, Rohit ruled out of second Test|
|Kovac: Ajax-Bayern draw was amazing|
|Sims re-signs with Dragons until 2022|
|Derrius Guice injury update: Redskins RB (knee) has rehab setback, undergoes 3 more procedures|
|Emery: Arsenal could sign defender in January|
|Phillies sign McCutchen to three-year deal|
|O´Neal thinks his Lakers teams could ´easily´ beat Warriors|
|A-League to add two clubs by 2020|
|Curry says he was ´obviously joking´ about moon landing comments|
|Now the beautiful part starts – Ronaldo ready for Champions League knockout stage|
|Bayern have a lot more potential – Lewandowski not satisfied despite top spot|
|Lyon star Fekir shares plaudits for Champions League progression|
|Mourinho not surprised by United´s defeat to Valencia|
|Motivation no issue for Benfica, claims Vitoria|
|Lewandowski finishes Champions League group stage as top scorer|
|Mourinho: We scored two goals and lost 2-1!|
|England have a diamond - Guardiola hails City´s Foden|
|Sterling´s carefree display invites us to love football more than others hate|
|Juventus achieved their objective, despite everything going wrong – Allegri|
|Never say never - Schmidt not ruling out All Blacks role|
|Bologna´s winning start ended in BCL|
|Di Francesco critical of Roma performance|
|Shakhtar Donetsk 1 Lyon 1: Fekir fires French side through in Group F|
|Benfica 1 AEK Athens 0: Grimaldo sends hosts out on a high|
|Young Boys 2 Juventus 1: Hoarau double seals famous victory|
|Manchester City 2 Hoffenheim 1: City through as group winners after Sane brace|