Why Rangers will always mean regret for Ferguson

Once the Glasgow side's record signing, United's manager has never forgiven his old club for his ignominious exit. Ian Herbert reports

Ferguson will play Rooney tonight (Getty Images)

Sir Alex Ferguson has one eye on November's return fixture at Ibrox already, not least because he has it on good authority that one of Walter Smith's assistants has a supply of his favourite Australian Shiraz, Penfold's Grange, in the cellar. "There'll be a glass of wine available in my office, win or lose," he says in tonight's programme notes. "No pressure of course, but we will be at Ibrox in November. Need I say more?"

Of course, that's not the only reason why Ferguson actually began discussing the visit to the oak-panelled corridors of Ibrox even before he discussed the home leg yesterday, reminding us that this Champions League encounter "does bring a bit of focus on me because I am Scottish and I played for Rangers".

It was 43 years ago this July that Ferguson received a knock on his front door as he watched athletics on television and opened it to the son of then Rangers manager, Scot Symon, who handed over his father's address and declared that his company was requested that same evening. Ferguson, then 25, signed for £65,000 – £10,000 more than the previous record between Scottish clubs – days later and believed his career was about to explode. That it did not has been a source of regret that he still cannot entirely dispel. Even in tonight's notes, he declares that, "For one reason or another I didn't have the greatest time there." One of the reasons, he has always believed, was the sectarian prejudice of a Rangers PR man Willie Allison, whom he accused of circulating whispers about his wife, the now Lady Cathy, being a Catholic. More prosaic explanations include the rapid replacement of Symon, whom Ferguson adored, with Davie White, whom he abhorred, and whose £100,000 signing of the Hibernian striker Colin Stein spelled the beginning of the end. Ferguson's final ignominy before leaving for Falkirk included turning out for Rangers reserves and even juniors side against Glasgow University and the local corporation's transport team. One of his reserve opponents in those days was an up-and-coming Kenny Dalglish.

So that's why this fixture really appeals, the chance to deliver another statement on a club which might now be managed by one of his oldest friends – Walter Smith was Ferguson's assistant with the Scotland side at the 1986 World Cup as well as the stand-in when Carlos Queiroz went to Real Madrid – but whose club Ferguson, with his elephantine recall of past wrongs, will never entirely forgive.

The prospect of revenge is diluted though, by the financial waters Rangers are thrashing through. Ferguson accurately stated a few years ago that his £65,000 move from Dunfermline to Rangers was worth about £6.5m in modern money but that kind of spending power is well beyond Smith, so constrained is he by Rangers' £30m debt and the determination of the club's new bankers, Lloyds TSB, to reduce it.

Compared with United's £716m debt, his old club's impoverishment seems laughably mild. "I couldn't believe Walter when he told me what the debt was," Ferguson admitted yesterday. "I find it really surprising he can't get the players he needs to keep Rangers at the very top end of the Premier League in Scotland. Celtic have spent quite a lot so it is a challenge for him to do it with more or less the same players. He is making a silk purse out of a sow's ear."

As the United manager's discussion of his clubs past and present continued it was hard to ignore the fact that their present battles are not worlds apart.

Ferguson maintained once again yesterday that United "have no financial restrictions". He also tantalisingly suggested that there was "one player" he would have bought this summer though "that move was sealed off quite early by the club he went to" – and was perhaps talking about Barcelona's David Villa, signed from Valencia. But there is no doubt that many of Europe's elite clubs have left his own behind with their spending. Ferguson portrayed his decision to invest in youth as one which would set the club up for the time when he is gone. "The best thing we can do until the market becomes more sensible is produce young players and buy young players and develop them," he said. "By doing that we are securing the next eight years easily at Manchester United."

Yet the average age of United's side at Goodison Park on Saturday was over 30 and the European campaign they are about to embark upon will reveal whether Ferguson's strategy really will enable the club to continue competing with Barcelona, Real and the other big spenders. Rangers should be comfortable opposition but the acid test will come next February.

United's defensive vulnerability this season has suggested they are no longer indomitable at the back, even though Ferguson rejected the suggestion that there are "frailties" there. He did admit that United are, this season as well as last, wasting opportunities – which may explain that move for Villa, if it was him. "[My players] are a bit wasteful in their chances," Ferguson said. "That has been the case in all our games this season and a few last year."

The obvious conclusions being that the trials and tribulations don't stop in football, even when the misery of life in Rangers reserves seems a lifetime back and that some of Ferguson's toughest times in management may yet lie ahead. Wins tonight and at Ibrox will be enjoyable distractions, just like the Shiraz. Something to help keep the demons at bay.

THREE KEY CONFRONTATIONS

Rio Ferdinand v Kenny Miller

Miller has form against United, scoring a winner for Wolves in 2004, and Nemanja Vidic will beglad to have Ferdinand back in the heart of defence after Jonny Evans' shaky start to the season. The returning Ferdinand will be confident of a clean sheet against a Rangers team who have not won in their last 10 Champions League games.

Darren Fletcher v Steven Davis

A further home nations clash in the centre of the park with a Scotsman facing a Northern Irishman. With both in top form for their club this match-up could shape proceedings. Davis willneed to shackle United's midfield but Walter Smith has had a tendency to play Davis wide right, which could limit Rangers' chances of pulling off a shock win.

Wayne Rooney v David Weir

At 40, Weir could be something of a liability at this level, especially considering the pace ofthe United attack. Rooney has scored 21 goals in the competition and will be eager to put his off field problems behind him and kick start his season against a Rangers team who conceded 12 goals in their six group games last season.