After a largely demoralising summer, which began with being pipped to the William Hill Premiership title by Celtic in May, 1,300 embattled Jambos travelled to the Portuguese capital for one of the most formidable fixtures in the club's recent history, braced for a fourth consecutive defeat under new head coach Wouter Vrancken.
And that was exactly what transpired as Marco Silva's Benfica opened the scoring in the third minute, led by three at the break and then added another three in the second half to remove all sense of jeopardy from next Thursday's second leg at Tynecastle.
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While the Portuguese giants are on course to face the losers of the Champions League tie between Aarhus and Sabah Baku in the Europa League play-off round, Hearts are staring at a likely Conference League play-off against Rapid Vienna, who lead Paide 4-1 after the first leg in Estonia.
Hibernian will take a valuable lead to North Macedonia for the second leg of their Conference League third qualifying round clash after overcoming Shkendija 2-1.
Hibs had gone in front in the 73rd minute through Owen Elding, only for the visitors to level less than three minutes later courtesy of Marko Gjorgjievski.
However, Warren O'Hora notched a 90th-minute winner when he bundled in a Jordan Obita corner to leave Hibs in a good position to reach the competition's play-off round when they make the trip to Skopje for the second leg.
Motherwell's impressive start under Alfred Johansson continued as they secured a 1-1 draw away to HJK Helsinki in the first leg of their Conference League third qualifying round tie.
The Lanarkshire side's new Swedish boss briefly looked on course for his fourth consecutive victory at the helm after Tawanda Maswanhise's penalty gave the Steelmen the lead just after the hour mark.
However, 36-year-old former Celtic and Norwich City striker Teemu Pukki equalised for Finnish side HJK within seconds of coming off the bench.
Motherwell, who lost Alex Lowry and Regan Charles-Cook to injuries in the closing stages, will return home believing they have a good chance of setting up a glamour play-off showdown with Europa League runners-up Freiburg later this month.
