Jose Mourinho and Fenerbahçe were left on Wednesday with a difficult final test in their quest to return to the Champions League, after his side drew 0-0 at home against Benfica in the first leg of their qualifying playoff.
The Yellow Canaries were unable to capitalize on Florentino's red card and the Portuguese giants, who lost in the last 16 last season to Barcelona, held on in the pressure cooker atmosphere in Istanbul.
A lackluster first half ended with visiting goalkeeper Anatoliy Trubin making two vital saves to deny Youssef En-Nesyri's header and Jayden Oosterwolde's strike from distance.
But Fenerbahçe were given a lifeline 19 minutes from time when Florentino first fouled Sebastian Szymanski before pulling back Talisca, resulting in his sending off.
En-Nesyri thought he had snatched the win late on when he headed home after Talisca's strike had been fumbled onto the crossbar, but the goal was ruled out for offside.
Benfica, therefore, have the slight edge going into the return in Lisbon, but Fenerbahçe are aiming to reach the Champions League proper for the first time since 2008/09.
Elsewhere, Celtic's Champions League hopes are firmly in the balance after they were held to a goalless draw by Kairat Almaty of Kazakhstan in Glasgow in the first leg of their playoff tie.
The Scottish champions pushed Bayern Munich close in the knockout phase playoffs last season after finishing 21st out of 36 teams in the league stage.
But Brendan Rodgers' team could not break down the champions of Kazakhstan, who have already come through three qualifying rounds to get to this stage and are eyeing a first ever appearance in the competition proper.
James Forrest was denied by a great save from Kairat goalkeeper Aleksandr Zarutskiy right at the start of the second half from one of few clear chances that fell Celtic's way at Parkhead.
At the other end, Brazilian Edmilson saw a chip from inside the centre circle for Kairat land on the roof of the net following a mistake by Celtic defender Cameron Carter-Vickers.
Daizen Maeda then found himself in behind the Kairat defence late on but could only shoot straight at substitute goalkeeper Temirlan Anarbekov.
Celtic therefore have it all to do when they make the daunting trip east next week to Almaty, not far from Kazakhstan's border with China.
"We're disappointed with the result and first-half performance. We didn't start with the intent and mentality we wanted to. We were quite passive," said Rodgers, whose team were booed off at full-time.
"There's no doubt we can go there and win. Of course, you want to take an advantage with you, (but) it's still very much in the balance."
Meanwhile, Norwegian champions Bodo/Glimt look certain to reach the league phase of Europe's elite club competition for the first time after a stunning 5-0 home win over Austria's Sturm Graz.
Kasper Hogh, Odin Bjortuft and Ulrik Saltnes all scored in the first 25 minutes for last season's Europa League semifinalists.
Hakon Evjen made it four early in the second half and a William Boving own goal completed the rout.
Swiss champions Basel drew 1-1 at home to FC Copenhagen in heavy rain at St Jakob-Park.
Xherdan Shaqiri's early penalty put Basel in front, but Gabriel Pereira equalised for the Danish side in first-half stoppage time.
Basel had substitute Jonas Adjetey sent off late on but held out for a draw as an Andreas Cornelius goal for Copenhagen was ruled out for a marginal offside.
