Ten-man Rangers suffered a third straight defeat without scoring after losing 3-0 at home to Napoli in the Champions League
The Group A clash turned, according to Rangers boss Giovanni van Bronckhorst, on James Sands' 55th-minute sending-off for a second caution after the defender brought down Giovanni Simeone to concede a penalty
However, despite recalled Rangers goalkeeper Allan McGregor, 40, twice keeping out penalties from Piotr Zielinski, the visitors finally made the breakthrough midway through the second half via a third spot-kick, successfully converted this time by Matteo Politano
The Serie A leaders sealed the victory with two late goals by substitutes Giacomo Raspadori and Tanguy Ndombele as they maintained their unbeaten start to the season
For Van Bronckhorst's side, however, this was a third consecutive defeat in all competitions as they remain rooted to the bottom of Group A ahead of back-to-back games with Liverpool
Rangers headed into this clash on the back of bruising 4-0 losses to Celtic and Ajax, leading Van Bronckhorst to make five changes against one of Europe's most in-form teams
One of those changes saw a first start in attack since March for Alfredo Morelos and the move almost paid immediate dividends when the striker headed narrowly off target straight from the kick-off in what was a pulsating start at Ibrox
The impressive Zielinski curled an effort against the outside of the post just seconds later, but it was the hosts - perhaps spurred on by a rousing pre-match rendition of the national anthem, against UEFA's wishes - who looked the more likely to score in the opening exchanges as Scott Arfield also went close
Napoli, however, slowly grew into the contest as Rangers' recalled veteran 'keeper had to be quick off his line to deny Simeone, and somehow it was still scoreless at the break
Ten minutes after the interval, though, came the defining moment of the game as Simeone - son of Atletico Madrid boss Diego - burst through on goal, only to be brought down by Sands' desperate lunging tackle from behind
Zielinski's first effort was kept out by McGregor, before Politano converted the rebound, only for it to be re-taken after the Video Assistant Referee spotted the scorer encroaching in the area
Incredibly, McGregor again guessed right to stop the Poland midfielder's spot kick, however, the visitors were then awarded a third penalty when Borna Barisic was deemed to have handled Kvicha Kvaratskhelia's shot in the box
This time it was Politano who was given the responsibilities, just about beating McGregor low down to his left, before Napoli rounded off the game with two late goals
Raspadori nipped in to score their second with five minutes left, then Ndombele - on loan in Naples from Tottenham - swept home the third in stoppage time
Rangers entered their clash with in-form Napoli having lost their previous two games to Celtic and Ajax 4-0, results that produced much soul searching from manager Giovanni van Bronckhorst
The Dutchman's response was to double down, insisting he had no intention of changing his footballing philosophy simply on the basis of those two, albeit, painful reverses
And while his side did lose again, without scoring, to the Serie A leaders at Ibrox - just the second time they have suffered defeats in their opening two Champions League group games - it was a much-improved display from the hosts
In fact, Rangers were unfortunate not to go in ahead at half-time and despite having to play most of the second half with 10 men, they still mustered 10 shots in the match, six more than they managed against Ajax in their opening group-stage match
Now all they need to do is find the back of the net in their next group contest, at Anfield on October 4
"Until the red card we gave Napoli a really tough game," he said
"We were organised, good in the game and players were giving everything to get a good result
"We created chances to open the scoring and it was a nice battle to see, but of course with the sending off we knew it was going to be difficult
"Allan saved the penalty twice which was fantastic but the first goal we conceded made me change the way we were playing because we need to attack and you know you are going to get more space, so in the end I think the 3-0 defeat did not reflect the difference in quality
""After two missed penalties it was important that we kept going," he said
"They started really strong with their fans as we expected but instead of shrinking we reacted I felt
"I thought it was a balanced game at a lot of points but we didn't change, we never stopped pressing them and I want to thank everybody
 It was another good game for me to be on the bench
"Napoli have had to cope with losing a whole host of superstar players of late, however, one man they will be glad to keep hold of is their Poland international
The 28-year-old, who has been in Naples since 2016, ran the show at Ibrox on Wednesday night, displaying some excellent touches and close control that the hosts could not live with
Everything that was good from the Serie A leaders emanated from his boot and while he did spoil his performance by having two penalties saved, it did not end up costing his team as they ran out comfortable 3-0 winners
Rangers take on Dundee United at Ibrox in the Scottish Premiership on Saturday afternoon, with the game kicking off at 3pm
Meanwhile, Napoli face AC Milan at San Siro in Serie A on Sunday at 7
45pm
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