29. Neil Webb

Signed from: Nottingham Forest (£1,500,000), July 1989
Debut: 4-1 win vs Arsenal (scored once), August 19th 1989
League Record: 70 games (+5 as sub), 8 goals
Sold to: Nottingham Forest (£800,000), November 1992

There’s a firm memory in my head of the morning after the opening day of the 1989/90 season. United had just smashed the previous season’s champions Arsenal 4-1 and, reading the match report in the Sunday paper at my granddad’s house, I marvelled at what seemed a new dawn with our all-star midfield duo of Webb and Robson.

Ah, youthful naivety. Webb would become one of the most reviled United players of his time but it’s worth remembering just how good he was: he was a top player at Forest and the fee we paid didn’t seem that much given the quality he was know to have. After serving time at both Reading and Portsmouth, it was Clough who took him to the top level and it wasn’t long before he became the 1000th player to be capped for England.

By the summer of 1989, he was on the verge of being fully established alongside Robbo for England where he was expected to star in the following year’s World Cup. We stumped up the cash, and on his debut he smashed in a brilliant goal. As debuts go, it didn’t get much better and the crowd must have been buzzing.

Only a matter of weeks later, a tackle caused serious damage to his cruciate ligament. He was out of action for most of the season and though he was back for the FA Cup final and set up the winning goal, he was never the same player again. Always a tad chunky, the injury robbed him of the speed to compensate. Though he still somehow made the World Cup squad, he only got match time in the very sedate third/fourth place play-off game.

In 1990/91, he played plenty of games but the performances weren’t up to his previous standards and there was also plenty of competition for places - his lack of form might be reflected in his scoring record seen above, compared to 47 goals in 146 games for Forest. Though he played in our unsuccessful League Cup final team, he was left out for the Cup Winners Cup final months later. Matters reached a nadir a year later in a game against his old team: with United losing and needing a win to try to get a league challenge back on track, he was subbed. Rather than race off to get the fresh legs on the pitch, he trudged off at a pace that suggested he didn’t give a toss. He wouldn’t be forgiven, and though he somehow made it to the European Championship fiasco in Sweden that  summer, his United career was essentially finished.

Somehow, we managed to flog him off back to Forest for a decent fee, perhaps one of the many signs Brian Clough was seriously beginning to lose it. He was perhaps at his level helping Forest gain promotion back to the top flight in 1993/94, and subsequently saw out his playing days with Grimsby Town and Aldershot. (In)Famously, he later worked as a postman, for which he was the target of an unfair amount of ridicule but has since found employment as a pundit and coach.

28. Mike Phelan

Signed from: Norwich City (£750,000), July 1989
Debut: 4-1 win vs Arsenal, August 19th 1989
League Record: 88 games (+14 as sub), 2 goals
Sold to: West Bromwich Albion (free transfer) May 1994

Into a new season, then. Following a 1988/89 season that defined "mediocre", Fergie brought out the chequebook to bring five new names to the club. Of which the first one we'll come across is Mike Phelan. He was an odd signing on some levels, paying a fair sum of money for a player who was hardly dynamic even in his best years at Norwich. Essentially, I think we were buying a younger version of Mike Duxbury. 

For his first two seasons, Phelan mainly played in a midfield that was often lop-sided due to our lack of a right winger, a job which would sometimes fall to Mike, which seems laughable in hindsight, given he had a chronic lack of pace. I can only assume there was nobody else to do the job after we’d flogged Gordon Strachan and Fergie lost faith with Russell Beardsmore. Mercifully, the emergence of Lee Sharpe meant most of the play went down the other flank. That said, it was our man here who set up Mark Robins to score the memorable winner in the 1990 FA Cup semi-final. Phelan wasn’t a terrible player, and often did his job competently enough, but the feeling was that he wasn’t going to play a big part in winning the big prizes. 

With subsequent signings of other players and the appearance of some kid from Salford, he ended up spending the next two seasons as a classic utility player, often filling in at right back. In our first Premiership winning campaign, he just played enough games for a medal, and even scored his first ever goal at OT during a FA cup game vs Bury, but barely featured the next season and was binned off to WBA on a free. 

As a player, he was solid enough but never the kind of quality that wins leagues – for one thing, he never scored anywhere near enough. He also had a moustache, and I have a problem taking footballers with muzzies seriously. On the plus side, he had an ace chant to the tune of the Righteous Brothers’ classic: “You’ve lost your hairline, Phelan...” 

For several years, he worked back at United as an assistant manager and the target of no shortage of ire from some sections of the support, as well as being the source of much amusement for his taste in training shorts. 

21. Ralph Milne

Signed from: Bristol City (£175,000), November 1988
Debut: 2-2 draw vs Southampton, November 19th 1988
League Record: 19 games (+4 as sub), 3 goals
Sold to: Sing Tao of Hong Kong (free transfer), summer of 1991

Often brought up in "Worst United Player" polls, Ralph Milne was a gamble by Fergie to fill the left-wing space until Lee Sharpe was ready. It didn't work, but the small fee perhaps warranted the risk.

After all, at his peak, Milne was part of a Dundee United team that won the Scottish championship and were becoming a force in European football. In his best years, he was scoring for fun in domestic and continental competitions and to this day is highly rated by fans in that part of Scotland.

It all went downhill fast though, for whatever reasons and his powers were well on the wane by 1988. Indeed, we signed him from Bristol City, who were then in the third tier of English football. He'd come to England to sign for Charlton but his form for them had caused the drop down. Fergie obviously remembered Ralphie from his glory days and after flogging Jesper Olsen, needed a replacement.

United fans, understandably, were underwhelmed. Used to erratic but talented wingers like the Dane and Gordon Hill, the slower style of Milne was never going to go down well. He had the odd moment, but wasn't able to inspire a struggling team and after the end of the 1988/89 season, he made only one appearance off the bench the next year, spending the best part of two campaigns dossing round the reserves, with the exception of a short spell on loan down at West Ham.

Fergie reckons Milne couldn't handle the sheer pressure of playing for United, which may be true, but he perhaps should have judged that Milne wasn't a big club man. After he left, according to Lee Sharpe, he sold a story to the tabloids about players getting off their kites in Amsterdam during our trip over to Holland for the European Cup Winners Cup final in 1991 - thanks for that Ralphie!

19. Mal Donaghy

Signed from: Luton Town (£650,000), October 1988

Debut: 1-1 draw vs Everton, October 30th 1988
League Record: 76 games (+13 as sub)
Sold to: Chelsea (£100,000), August 1992

One of those players you forget played for us until you're reminded, Mal Donaghy is perhaps better regarded by fans of Luton Town, with whom he was a consistent performer throughout most of the 1980s.

Perhaps it was seeing him play his part in their 3-2 victory over Arsenal in the 1988 League Cup final that inspired Fergie to cough up a then not-inconsiderable sum to bring him to Old Trafford. Curiously, he'd allowed Kevin Moran to leave on a free only a few months before, which makes me wonder why we went and spent so much on a defender only a year younger at 31.

Moran, of course, was a crowd favourite due in no small part to his at-time insane bravery: he famously smashed his head in the 1983 FA Cup semi-final against Arsenal, and was carried off on a stretcher, blood pouring out from the wound while pumping his fist in the air towards the fans.

What Donaghy (who made over 90 appearances for Northern Ireland, including in the 1982 and 1986 World Cup finals) had going for him was that he was rarely injured and could play anywhere across the back four. In his first season, he played most games alongside Steve Bruce in the middle but from then on took on a utility role, filling in where needed without being a first choice again.

Thing is, I have two clear memories of Mal. The first is in the semi-final of the Cup Winners Cup against Legia Warsaw - the first leg in Poland being a game I seem to recall being on around 3/4pm our time, as I was watching it after getting home from school. They scored first before McClair quickly equalised. With Warsaw on the attack, Mal made a crunching tackle on their right winger, and fed the ball to Mark Hughes, who drove through their defence before smashing in a low drive from the edge of the box. Steve Bruce scored a third to create plenty of breathing room for the second leg, a 1-1 draw. For that challenge, Donaghy earned his winner's medal for sitting on the bench in the final in Rotterdam.

However, the next year he made a serious arse of himself in a game against Chelsea, at a time when we were chasing the title. Under no pressure whatsoever, he played pass back without (I assume) checking where his teammate was. The result was a somewhat horrific own goal, and a 1-1 draw at a point where we were struggling for points. It's that memory that taints my feelings for the guy, though his solid, unspectacular style doubtless didn't endear him to my young mind.

That summer, Mal was binned off to Chelsea, where he played regularly for a couple of years before retiring. He's currently coaching the Northern Ireland under-19 team.

9. Peter Davenport

Signed from: Nottingham Forest (£570,000), March 1986
Debut: 1-0 defeat to Queen's Park Rangers, March 15th 1986
League record: 73 games (+19 as sub), 22 goals
Sold to: Middlesbrough (can't find evidence of the fee), November 1988

Signed by Big Ron in the Spring of 1986, at the point where the wheels hadn’t just come off the title challenge wagon but had overtaken us and were lying at a heap at the bottom of the hill. He was brought in to try and score the goals after we’d arranged for Mark Hughes to be packed off to Barca, leaving the latter's mind somewhat off the ball.

Wirral lad Davenport wasn't the first attempt at this. Months before, Terry Gibson had been signed from Coventry City, where he had scored plenty of goals in a struggling side. However, Gibson had even less luck, only scoring one goal before Fergie packed him off back to that London, where he played for Wimbledon in their amusing 1-0 defeat of Liverpool in the 1988 FA Cup final.

Davenport, meanwhile, was seen as the latest in a succession of players who were brilliant for Nottingham Forest but failed at United: Ian Storey-Moore and Garry Birtles were the original sinners, although Moore was desperately unlucky both with his injuries and that he was playing in a dire team bound for relegation. The curse would only be lifted, of course, with the signing of a young lad from Cork many years down the line.

As noted above, Davenport was a very good striker at Forest, good enough to win an England cap as sub against Ireland, where he had enough time to tee up Gary Lineker for his first international goal. In a series of events that rarely (if ever?) happens these days, he'd arrived at Forest as a 20-year-old from non-league Cammell Laird, having failed a trial at Everton.Within a matter of months, he was playing top flight football and banging in a hat-trick against Ipswich.

With 118 games and 54 goals in the bag, he was sold off to us, apparently to pay off repayments on a stand. £570,000 must have seemed a reasonable fee at the time, but Handsome Pete, like Birtles, failed to get out of the blocks, with only one goal in 12 prior to the end of the 85/86 season. And even that was a penalty.

1986 may well have been United’s worst calendar year since relegation – mercifully Big Fat Ron was sacked in November and Govan’s finest brought in to stop the rot, with the team picking up to achieve mid-table safety in 1986/87. Davenport was actually top scorer that campaign, but Fergie had obviously seen enough and Brian McClair was snapped up to lead the line.

My own actual memories of Davenport at United are very limited. The stats show he had a short run of form, scoring in three consecutive games against Luton, West Ham and Rotherham (the last one in the League Cup) before losing his place. He put in a transfer request and we binned him off to Middlesbrough, only for him to come back to haunt us by scoring the winner a few months later at Ayresome Park – a game amazingly played 24 hours after our 3-1 victory over champions Liverpool on January 1st. For that goal alone, he gets the tag below.

Despite that moment, he never really cut it as a top striker again, either on Teeside or up the road at Sunderland - he also had the misfortune of relegation with both teams. He later rocked up playing for the Mackems in the 1992 FA Cup final and I seem to recall him playing for Airdrie in Scotland. The last few years have seen him undertake several non-league coaching/management roles.

1. Jim Leighton

Signed from: Aberdeen (£500,000), June 1988
Debut: 0-0 draw vs Queens Park Rangers, August 27th 1988
League Record: 73 games
Sold to: Dundee (£200,000), February 1992

We start with a #1 making his first appearance for United on the opening day of 1988/89 and who may well wish he’d never signed for us.

On the face of it, Jim Leighton must have seemed a sound signing: experienced at the highest level at both club and country, he’d won European honours with Aberdeen (then managed by Alex Ferguson) and been Scotland’s man between the sticks for the 1986 World Cup, having also gone to the ’82 finals as their third choice. Indeed, so well regarded was Leighton that even Jimmy Greaves dropped his usual “Scottish goalie = butterfingered clown” routine when talking about him.

He came straight in as first choice, with his predecessor Chris Turner being packed off to Sheffield Wednesday (subsequently to have some revenge in the 1991 League Cup final) and young Gary Walsh struggling with fitness. Initially, he must have thought he’d made a smart move: the previous season (87/88), United had come second behind a dominant Liverpool side but had made what seemed astute signings in him and Mark Hughes.

But it never happened. The side struggled to catch any consistent form, even at one point going six games without scoring – though it’s fair to say the problems weren't with the goalkeeper. Things took a downward turn the following season, though, and Leighton became a target of ridicule from the fans, which won’t have helped his confidence.

One positive was a decent run in the FA Cup. I can remember the semi-final against Oldham Athletic clearly, and Jim didn't look at all assured – though my main memory was the unfortunate sight of him having to change his shorts. We made the final, after a replay, to face Crystal Palace, managed by former United winger Steve Coppell. Famously, Leighton had a nightmare as we were lucky to sneak a 3-3 draw.

Action was needed and we saw the first instance of Ferguson’s necessary brutalism. Leighton, the man he’d brought through the youth ranks at Aberdeen, playing in the World Cup for Scotland and signed for big money, was dropped. The gambit worked, but Leighton cut a sorry figure in his suit before the game and was nowhere to be seen in the pictures of the post-match celebrations. The next season, he was essentially third choice keeper and only got a run out in a League Cup tie against lowly Halifax Town.

In 1992, he drifted back to Scotland with Dundee before a move to Hibs saw him return to the kind of form that made his name. Despite being in his mid-30s, he re-established himself as Scotland’s first choice goalie throughout the late 90s, playing in the 1998 World Cup. These days, he’s back up in Aberdeen (where he returned for a short spell at the end of his playing career) as a coach.

Jim Leighton was a more than capable goalkeeper, not helped by playing for United in the period before it all clicked for Ferguson. He’ll not be the first big name we’ll see to fail at Old Trafford.