It was a poor Rangers performance as they struggled all night to find a glimpse of the free-flowing football which had destroyed Dundee United at the weekend but they made it and that is the main factor.
The passing was slack, the movement was slow and the creativity just was not there against a side who were little more than hard battlers. However, the Anzhi saga is now over.
It was largely a step into the unknown for Rangers as they knew so little about the Russians and perhaps that explained their tentative start to the game. There was no real conviction about their play and that only heartened their opponents.
Advocaat sent out the same side which hammered Dundee United with the clear aim of trying to get at Anzhi as early as possible but the players failed to get the early advantage they wanted and it boosted the Russians’ confidence.
There was an early opening for Fernando Ricksen when Russell Latapy’s fourth minute freekick broke nicely to him just outside the box but the Dutchman completely miskicked and the chance was lost.
Ricksen again found himself in space in 13 minutes when Ronald de Boer found him with an excellent pass but his shot was weak and keeper Alexandr Zhidkov was able to save easily.
Another exquisite touch from de Boer almost produced the opening Advocaat craved in 16 minutes. Spotting Barry Ferguson running into the box, the Dutchman back-heeled the ball into his path but the skipper go under his shot and the ball sailed over the bar.
Advocaat knew that a goal at this stage would have settled his side and de Boer again did his best to try to supply it in 24 minutes. This time a lovely feint gave him space on the left for a cross which he duly drove low and hard towards the edge of the box where Latapy was waiting.
The little Caribbean star hit the ball sweetly enough with his left foot but Zhidkov was equal to it, diving to his left to push it away for Rangers’ first corner.
The save seemed to inspire the Russians who start to cause Rangers some problems which caused some alarm on the bench, although Stefan Klos was not under any pressure.
It was frustrating more than anything else for Rangers because it was clear that they were a better side than Anzhi but they could not make their superior ability count. Perhaps that frustration was borne out when Ricksen was booked for a clumsy foul on Anzhi captain Narvik Sirkhaev.
Even when they did manage another shot on target – in the 37th minute – Zhidkov proved a more than capable goalkeeper. De Boer won a freekick five yards outside of the box and touched it to Neil McCann who slammed a left foot shot which the Anzhi keeper blocked very competently.
Then just before half-time McCann’s corner from the right was nearly flicked into the Anzhi net by Magomed Adiev, but Andrey Gordeev was on the line to head the ball clear.
Rangers needed to do something to inject some life into their play and Advocaat opted for the same tactical switch he employed at Tannadice, moving Latapy into a more central area but there was little return early on.
Rangers seemed unable to control the midfield area while up front Tore Flo was simply having an off-night and was unable to find any space to hurt the Russians. It was no real surprise when he was taken off in 58 minutes and Claudio Caniggia was sent into the contest.
Five minutes later Advocaat made another like for like change when he brought on flying Dane Peter Lovenkrands for McCann, hoping that Lovenkrands’ pace would produce something tangible.
He almost got the payback within two minutes when Ferguson sent Lovenkrands away down the left but the Dane overdid the cross which was beyond de Boer.
It was such a slog for Rangers and just what they did not want with such a huge game against Celtic on Sunday and hard to understand when the game held such importance.
The incision and creativity Advocaat demanded was just not there and the situation became more and more nervous as the clock ticked down.
However, with just five minutes remaining Rangers finally ended the agony for their manager and their supporters and it was Bert Konterman who proved to be the hero with the goal that took them through.
That said there was a large slice of luck about the strike, but Rangers could not have cared less. They were through and that was the only thing that mattered.
Caniggia won a freekick on the left side of the box. Numan worked the ball square for Konterman who slammed a right foot shot which took a wicked deflection off Andrey Gordeev to flat foot Zhidkov and send the ball flying into the right corner.
The relief in the Polish Army Stadium among the 1000-strong Rangers supporters was tangible. Advocaat knows it was a far from acceptable performance but his team is in Friday’s draw and that’s what counts.
FC ANZHI MAKHACHKALA: Zhidkov; Yaskovich, Gordeev, Agalarov, Sirkhaev, Adiev, Ramazanov, Akaev (Nicolic 89), Bilong, Edu, Tysmbalar. Subs not used: Holly, Ngangue, Ivanov, Hoshic, Alekseev, Armishev.
Bookings: Tsymbalar (53)
RANGERS: Klos; Ricksen, Moore, Amoruso, Numan; Latapy (Hughes 90), Konterman, Ferguson, McCann (Lovenkrands 63); de Boer, Flo (Caniggia 58). Subs not used: Dodds, Kanchelskis, Vidmar.
Bookings: Ricksen (30)
Ref: Edgar Steinborn (Germany)
Att: 3,700.
Man of the match: Ronald de Boer
Moment of the match: No question, big Bert’s winning strike.