The installation of an artificial pitch in the summer of 1985 was warmly greeted initially by the footballing press but gradually mutterings of discontent grew and by the time the Town went back to grass in 1991 they had reached a crescendo. Also unpopular was the decision to ban away supporters in the wake of damage caused by so-called Millwall supporters in an FA Cup match at Kenilworth Road.

Perversely, it was during this period that the Town enjoyed the most successful period in their history. A position of ninth in the table was reached in season 1985/86 at the end of which David Pleat found the call of Tottenham too great and he departed amid much acrimony.

His replacement, John Moore - a stalwart defender from the Fourth Division days - led the Town to their highest ever placing in Division One of seventh in 1986/87 and then resigned due to his dislike of the high profile nature of the job. Moore's assistant, Ray Harford, was next in line for the hot seat and he presided over a momentous 1987/88 season which included three trips to Wembley as well as yet another FA Cup semi-final, this time against Wimbledon.

Defeat in the Simod Cup final, the Mercantile Credit Centenary Tournament and the FA Cup semi-final appeared to signal a season of glorious failure but on 24th April 1988, an army of 35,000 Luton supporters saw the Hatters win their first ever major trophy. A last-minute strike from Brian Stein saw the Town finally overcome Arsenal 3-2 at Wembley in a see-saw thriller in which Arsenal, leading 2-1, were awarded a penalty, which was brilliantly saved by Andy Dibble, before Town came storming back, leading to skipper Steve Foster lifting the Littlewoods Cup.