Nicky Law struck an extra-time winner as Rangers toiled their way to a 2-1 victory over Hibernian in the Petrofac Training Cup first round.
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The Englishman swept home 11 minutes into the first additional period after the Edinburgh side had done well to frustrate the hosts.
Lewis Macleod fired the Light Blues ahead after 14 minutes before some kamikaze defending allowed Danny Handling to level on the hour mark.
But the young striker's night ended on a sour note when he was sent off 11 minutes from time after thudding into David Templeton with an ugly tackle.
Rangers made their numerical advantage count in extra-time as Law's winner confined Alan Stubbs' to defeat in his first match in charge of Hibs.
Ally McCoist handed Kenny Miller and Kris Boyd their second Ibrox debuts as the Easter Road side returned to Ibrox for the first time since January 2012.
There was no Bilel Mohsni after his red card for headbutting Derby's Chris Martin on Saturday, so that gave the Light Blues' other summer signings Darren McGregor and Marius Zaliukas the chance to line up in defence.
Former Everton coach Stubbs, meanwhile, took over a threadbare squad after his predecessor Terry Butcher axed 15 players before being sacked himself. But he gave new recruits Mark Oxley, David Gray and Farid El Alagui their first starts for the Leith men.
It was another returning Rangers man, however, who scored the opener as Macleod raced on to a Lee Wallace cross, set himself, then fired under keeper Oxley.
Handling was allowed to level, though, when McGregor was caught out by David Gray's awkward cross. But after wasting three great chances, Hibs paid the price as Law struck the late winner.
It may be a new season, but the off-field problems at Ibrox refuse to go away. The summer saw sections of the frustrated Light Blues support call for a boycott of season tickets as their feud with the club's board rumbled on.
Season tickets were not valid for Hibs' visit, but there was clear evidence that fans were staying away as just 18,138 turned out for the opening game of the campaign.
The League One champions cantered to the third-tier title unbeaten last season, but they were painful to watch at times.
At first though, it looked as though the re-introduction of Boyd and Miller would give McCoist's team a more threatening look.
Boyd's first effort after five minutes was blocked by Jordan Foster, while the former Kilmarnock man saw a second effort ruled out soon after Macleod's opener when referee John Beaton blew for handball just as his strike hit the net.
A Miller snapshot after 27 minutes was beaten away by Oxley, but the reunion of the former Scotland duo's partnership was not the cure for all Rangers' ills.
As the tempo dropped, Hibs gained a foothold. Handling whistled a shot just wide two minutes after the break, while a second chance went a begging when Sam Stanton fired tamely at Cammy Bell after Liam Craig's superb pass sent him galloping in on goal.
Rangers were playing with a five-man midfield, but they were struggling to find blue shirts with their passing.
It was Zaliukas who lost possession on the hour mark and Handling made him pay as he fired home from six yards after Gray's cross fell at his feet after spinning off McGregor.
There was chaos in the Rangers area moments later when McGregor raced out as Craig clipped a ball into the box. Zaliukas remained rooted to the spot, though, as he played El Alagui onside.
But the Moroccan blew his chance as he volleyed over, then wasted another effort as he was high with a three-yard header from Stanton's corner.
McCoist had switched to a back four as he replaced McGregor with Templeton and the winger's introduction at least gave them a man advantage when he lured Handling into a stupid challenge with 11 minutes left to earn an immediate red card.
Rangers had endured extra-time misery as they lost to Raith Rovers in the final of last term's competition. But, with the extra man, there was no repeat as Law curled a low shot round Oxley's reach to seal victory.