When Swindon midfielder, Alan McLoughlin, shimmied his way past two Saints’ defenders and then slid the ball into the net, to open the scoring in a Littlewoods Cup-tie in January 1990, he gave Chris Nicholl something to think about.

Come the summer, Alan was included in the Republic of Ireland’s World Cup squad. Still, Nicholl bided his time but, in December 1990, he paid a Southampton record of £1m (£700,000 up-front, plus £300,000 after 30 appearances) to bring Alan from the Second Division to the First – sheer profit for Swindon, who had acquired Alan, as a 21 year-old Mancunian (he went to school with Noel Gallagher), from his home-town United on a free transfer. Nicholl played his new man for the rest of the season, but it wasn’t where Alan wanted to play.

His favoured position was “in the hole”, behind two strikers, but that position was not available at Southampton, where a three-man front line of Matt Le Tissier, Alan Shearer and Rod Wallace was driven by a three-man midfield, in which the fulcrum was Jimmy Case. With Barry Horne playing wide-right, the only space for McLoughlin was wide-left.

Case would soon miss a few games and Glenn Cockerill would join the midfield. Alan would now get the occasional chance to burst through the middle, giving the fans a reminder of his old, Swindon-self. The fans should logically have been treated to much more of that in 1991-92. Nicholl and Wallace had both gone in the summer. And when Ian Branfoot took over, he got rid of Case. The stage was set for a 4-4-2 formation – or even 4-3-1-2, with McLoughlin in the hole – but Alan was not in Branfoot’s opening-day line-up at all.

He took issue with that decision and would never start for the Saints again. His Southampton season consisted of two games, coming off the bench. The second of those substitutions brought his Southampton appearances to 30. But it seems that either his three substitute appearances in Cup and League or his start in the Zenith Data Systems Cup did not satisfy the definition in the transfer-deal. Which meant that, when Branfoot sold his reject to Portsmouth,

Southampton could pocket the whole £400,000 transfer fee – but Pompey had an absolute bargain.

Alan’s 354 appearances for Portsmouth, where he brought his tally of Ireland caps to 42, suggest that, while Nicholl had merely misused his investment, Branfoot had utterly squandered it. After Pompey, Alan had another 40 League games left in him at Wigan and Rochdale. A persistent back-injury obliged him to quit playing in 2003 and to move into coaching with Conference side, Forest Green Rovers.In 2006 he was a live summariser, on Portsmouth matches, for local radio. Having then joined Pompey’s coaching staff, Alan was given leave of absence, in October 2012, for surgery to remove a kidney and a cancerous tumour. As the treatment continued into the summer of 2013, Alan reported that he had found it “tough”, but it was “going well”. He left Portsmouth with some bitterness in December 2014 after a restructuring of the backroom staff. He then moved to Swindon where he enjoyed a short commute to work where he managed the Robins’ academy, but in May 2021 the cancer he had fought for so long finally claimed his life, aged just 54.