A season that gave Alex McLeish so little joy, and was ultimately his last at Ibrox, provided one of the achievements of his Rangers career.

As pressure built domestically, a trip to Porto looked like the last thing that McLeish needed as the midway point approached during the 2005-06 campaign. The memories of that night are fond for the Treble-winning boss, though.

McLeish would end that term empty-handed as early exits from both cup competitions were followed by a third place finish in the Premier League.

But he still wrote his name in the history books as Rangers became the first Scottish club to qualify for the knock-out stages of the Champions League. A 1-1 draw at home to Inter Milan on the final night in Group H was enough to secure second spot and a place in the last 16 for the Light Blues.

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But it was the game a fortnight earlier that kept the dream alive as a depleted Gers side somehow earned a share of the spoils at the home of their Portuguese hosts.

McLeish said: “I remember it well. We were staring into the abyss and we came out with an amazing result. We had a real skeleton crew of a squad because we had a load of injuries that season and guys like big (Dado) Prso were missing.

“I had to bring a young boy in Ross McCormack off the bench to get us the equaliser and help get us to the last 16 of the Champions League. Porto were a hell of a good side and we weren’t given a prayer.

“We had a very inexperienced side, a lot of players that probably wouldn’t have played if the first selection had been available but they did the club proud.

“We had to hang on but you need to do that sometimes by the skin of your teeth. It was certainly a night that we will never forget.

“Yeah, it was tough and you had to try and take yourself away from wasn’t within your control and try and concentrate as much as possible on the players that you have at your disposal.

“It was out of our control in terms of the injuries but it can help you, it was a great night for my managerial career in terms of what you can learn from it. That was probably one of my best in terms of tactics that night.”

Rangers will return to the Estádio do Dragão on Thursday evening and boss Steven Gerrard would surely settle for the same outcome as the one that his predecessor achieved 14 years ago.

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It is Europa League qualification that is the ambition for Rangers this time around and Group G, which also includes Feyenoord and Young Boys, is finely poised after all four sides won one and lost one over the first two rounds of fixtures.

Rangers’ defeat in Bern last time out was only the third Gerrard has suffered in Europe in 24 attempts and McLeish is encouraged by the way the Light Blues have performed on the continent over the last 18 months.

McLeish said: “A 1-1 draw wouldn’t be the worst result this time around and they seem to be having a good run in Europe and they are comfortable in Europe, even though they lost against Young Boys.

“That was a wee setback for them and Porto is not an easy place to go to. They will be smarting from the fact that they are not in the Champions League this year and they have got a bit of rebuilding to do as well.

“It is a great record [Steven has] and it goes to show that he is a smart guy that has learned a lot through his career as a player and from the coaches that he has had over the years.

“He played a hell of a lot of times in Europe as a player and he gathered all that experience, plus what the managers have given him, and he is using that very well tactically.”

If Rangers could achieve their European ambitions and advance out of Group G, it would be another impressive accolade to add to Gerrard’s growing record at Ibrox.

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McLeish was back in familiar territory earlier this month as he took charge of the Rangers Legends side. Liverpool, with Gerrard as captain, were the opponents before the 39-year-old made a late cameo in blue to delight the home crowd.

It gave the former Scotland boss a chance to get a feel for the progress that has been made on and off the park in recent times but there is still considerable work to be done in the coming weeks and months.

It is the Premiership title and silverware in Scotland that are the ultimate aims this term. The balance, as McLeish knows, can often be tricky to strike week to week.

He said: “It is difficult because everyone expects you, as Rangers, to go into the midweek game and go and do what you do and play the same way as you play against a Premier League side in Scotland. You can’t do that.

“There was always a strategy, whether you waited on them or sometimes you go more attacking. There was a bit of canniness, in general, in the early exchanges of the game and you definitely didn’t want to go down in the first few minutes in Europe. It can become carnage.

“Steven has rebuilt the reputation in Europe and Rangers are a massive name that people will talk about wherever you go. It is only Rangers and Celtic.

“We regret that we don’t have a league where there are more teams up competing for the title, but even down south that is becoming difficult for top six teams. Steven has shown his maturity in the way that Rangers have been playing.”