Derek McInnes's difficult start as Rangers manager grew even bleaker after his side were eliminated from the Europa League qualifiers, losing 3-2 on aggregate to Jagiellonia Bialystok. A 1-1 draw at Ibrox was not enough to overturn the deficit from a 2-1 defeat suffered in Poland the previous week.
There had been brief hope for the home support when captain Lawrence Shankland converted a penalty in the 19th minute to level the tie on aggregate. But Rangers could not hold on, with Jagiellonia's Nik Prelec scoring a deserved equaliser in the 65th minute that proved decisive. Despite McInnes shuffling his formation and personnel in search of a response, Rangers were unable to regain control of the match, and frustration boiled over among supporters, who booed the team off at full time.
The result means McInnes remains without a win in four competitive fixtures since taking charge following his move from Hearts in the summer. Rangers will now shift their European focus to the Conference League playoff round, where they will face Czech side Jablonec.
Elsewhere, Hearts exited the Europa League but did so with their heads held high after a spirited 1-1 draw against Benfica. Having been thrashed 6-1 in the first leg, the Edinburgh side gave their fans a moment of hope when Tomas Magnusson fired them into a shock lead in the 77th minute. However, the celebrations were short-lived, as Benfica's Dodi Lukébakio restored parity less than a minute later, sealing a comprehensive 7-2 aggregate victory for the Portuguese giants, who had made seven changes from the first leg.
Despite the aggregate defeat, the performance under manager Wouter Vrancken was viewed as an encouraging sign, and Hearts will now turn their attention to the Conference League playoffs, where they are set to meet Austrian club Rapid Vienna.
Hibernian, meanwhile, secured passage into the same playoff round after grinding out a goalless draw away to Shkendija in North Macedonia, completing a 2-1 aggregate win. The match, played in intense heat at the Todor Proeski National Arena, was far from a spectacle, but Hibs manager David Gray praised his players for their resilience in testing conditions.
"I'm delighted for the players," Gray told BBC Sport. "It's a brilliant time to get your first clean sheet of the season."
He added: "I just said to the players, don't underestimate how big an achievement that is against a really good side who made it to the knockout stages of the competition last season. Added to that, the conditions, the heat, we had to deal with all these things. I don't think it was a brilliant game, but we put our bodies on the line and the attitude was there."
Hibernian will now face Belgian outfit Gent in the Conference League playoff round, rounding out a mixed night for Scottish football in Europe. While Rangers face renewed scrutiny over their stuttering start under McInnes, both Hearts and Hibernian can take pride in performances that, despite eliminations or narrow progress, showed fight against tough continental opposition.
Based on reporting from The Guardian.