Fenerbahce's flawless start to the new campaign came to a screeching halt on Saturday night as suffered a 3-2 home defeat to Trabzonspor.
The Istanbul giants game into the tie with an unblemished record of 19 wins from 19 games in all competitions but were undone by the resilient away side.
Former Southampton forward Paul Onuachu broke the deadlock after just 10 minutes before a quick-fire double from Berat Ozdemir and ex-Arsenal winger Nicolas Pepe put the tie out of reach just after the break.
To Fenerbahce's credit they mounted a respectable comeback as Saints and Ajax oldboy Dusan Tadic hit back with two goals from the penalty spot, either side of a Ismail Yutsek sending off.
Despite winning their first 10 league games, the defeat sees Fenerbahce fall behind Istanbul rivals Galatasaray, whose record stands at 10 wins and one draw from their opening 11 fixtures.
Coach Ismail Kartal, who returned to the Şukru Saracoglu Stadium for a third spell in the summer, and his squad packed full with plenty of familiar names to Premier League fans will be ruing their first dropped points of the season.
The home side were without the Brazilian midfielder Fred, signed from Manchester United at the start of the season, who has featured in 14 of those 19 games and provided five goal assists in a bright start to life in Turkey.
Up front, they have the former Chelsea man Michy Batshuayi, who joined last year and has scored four goals in their European campaign so far.
Batshuayi came off the bench on Saturday night but was unable to add to his tally. Another familiar name is the Bosnian, ex-Manchester City forward Edin Dzeko, signed from Inter Milan in the summer.
Dzeko may now be 37 but he's finding Turkish football very much to his liking
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