Former Villa boss John Gregory hopes his former club do not make the same mistakes which floored his old team’s title challenge 10 years ago.

Martin O’Neill’s class of 2009 kept up their unexpected and dogged pursuit of the leaders with Tuesday night’s 1-0 victory over Portsmouth at Fratton Park.

It left Villa sitting third after 23 games – precisely where they were under Gregory at the same stage in 1999, although Chelsea’s win over Middlesbrough last night pushed them down a spot to fourth.

There may be 10 years separating the two campaigns and a slight advantage to O’Neill’s crew – the 1999 lads had amassed 43 points at this stage compared to the 47 of their 2009 successors.

But otherwise there are strong echoes from the Gregory campaign. Similarly, his team was dominated by English players – in fact it was exclusively home based – with fears that the Villa of ’99 would be found out for a shortage of star quality and lack of strength in depth.

O’Neill knows the same whispers are abroad about his men, despite the signing of Emile Heskey, and fans are still hoping he will add to his numbers for the final months of the campaign.

Gregory, who ended a running feud with former chairman Doug Ellis over spending and ambition when he quit Villa in 2002, is full of admiration for O’Neill’s stewardship and envious of his relationship with new owner Randy Lerner.

But their campaign to establish Villa in the country’s top four – and claim that vital Champions League qualifying spot – still has a major test ahead, believes the man who led the club to the 2000 FA Cup final before leaving to mixed reviews from the claret and blue faithful.

Gregory said: “As I see it, there is one big test ahead for Martin. Each week Rafa Benitez and Fergie have to tell world class players, big stars, that they are not in the team- and cope with what comes with that.

“Martin is not yet in the same area. He may have to tell Craig Gardner he’s not playing, after the lad has done well for him but Craig is going to say ‘fair enough boss.’

“He has not yet got those big international players whose noses he is going to be putting out of joint, so I think the real test for Martin will come when he has to control big, big players.

“I don’t think he’s ever had that in his career, but that is what comes with being a manager of a top four team in England. David Moyes is much the same at Everton. Martin’s team still picks itself at the moment.

“He’s not a gambler, I don’t ever see him taking a risk, with the possible exception of Ashley Young. He buys tried and trusted players. But he’s got a chairman who lets him get on with it.

“With Doug, if you bought a player he had to be in the team. It would be ‘John, I’ve just paid £5m for him, why isn’t he playing?’ If somebody was earning £20,000 a week, then Doug could not accept somebody else earning £5,000 a week could be keeping him out of the side.

“Martin does not have that issue. He’s got a chairman who lets him get on with it and doesn’t want to get involved. He is in a fantastic position and that’s wonderful for Villa.”

Gregory and O’Neill would go on to dispute a League Cup semi-final in 2000, as managers of Villa and Leicester, when a solitary goal from Matt Elliott – now assistant manager at Halesowen -took the Foxes through.

It was yet another ‘nearly’ story for Gregory, but nothing quite defined his regime more sharply than the championship challenge that faded so drastically in the late winter and spring of 1999.

Villa, having lost star duo Dwight Yorke and Steve Staunton and having sold Savo Milosevic the previous summer, launched themselves into a club record unbeaten start and just like O’Neill’s men, doggedly chipped away.

Gregory, in his first major managerial posting, recruited Alan Thompson, Paul Merson, Dion Dublin and Steve Watson from the money Villa had stockpiled from their sales but it would not be enough to hold back the established forces.

Having been top at Christmas, Gregory’s team fell away badly thereafter and the former boss accepts his share of the blame, as well as lamenting Villa’s lost opportunity.

He said: “I was treading new ground and basically trying to survive. When I look back at it now, I was driven by self preservation as much as anything.

“Maybe, had I been a bit more adventurous with my selections, we would have won more of those games that we drew. But I wanted to make sure we didn’t get beat, which meant while we were not the most attractive team, you didn’t enjoy playing against us.

“I actually remember saying that year ‘you’re only ever one defeat away from a crisis in the Premier League.’ I’ve heard it said a lot of times since but that’s mine! It’s true. I felt the moment I lost a game, the press were on me.

“They are doing it now even more – ask Felipe Scolari. When that culture is about, you suffer from self doubt. I’ve since read that Brian Clough was riddled with self doubt, so do you think I wouldn’t be?”

But that still did not stop him battering away – fruitlessly – at Ellis’s resistance to ever more ambitious spending.

Gregory said: “I don’t want this to be me saying I never got any money, because I obviously did. But you always had a problem convincing Doug that from where we had come from, we needed more and that season bore it out really.

“Less than a year earlier, we had been 16th and now we were second, third in the table. But it was a perpetual source of tension between Doug and I. He always said that he would never let the club get into a financial mess, but I always felt we should recruit while we were strong.”

Villa paid for their lack of strength, as well as Gregory’s inexperience and self doubt, with the team limping into sixth.

He said: “Mark Bosnich had been brilliant before Christmas – I remember a performance at Coventry which was just incredible – but we lost him to long-term injury before Manchester United got ‘into’ him.”

“That match at Newcastle was another hammer blow, because Ugo’s eye socket bumped into Alan Shearer that night didn’t it? He was out after that and we couldn’t cope. When he just did what he was good at, there was no-one better than Ugo, a formidable defender.

“There had been a perfect relationship at the back with Gareth, Bozzy, Ugo and young Gareth (Barry) but that was broken up and we couldn’t cope.

“I hope the same doesn’t happen to Martin because Villa is and always will be so special to me. But the fans don’t need me to tell them how difficult it is going to be.”