The warning signs were there for Arsenal prior to the 1988 Littlewoods Cup final. Predicted by many to easily dispose of Luton Town in the Wembley showpiece, George Graham’s team were expected to maintain their grip on the trophy that they had won the year before against Liverpool. But history had proved that Arsenal had often not coped well with the tag of favourites.
Swindon, Ipswich, West Ham, and Valencia had all won finals against Arsenal that the north London club had been expected to win, yet the general consensus was that Graham’s rising stars would not allow Luton to be added to that list. After champions Everton had been knocked out in the two-legged semi-final, it appeared as if all the hard work had been done. What could possibly go wrong?
The story of how Luton upset the odds to win the 1988 Littlewoods Cup is a tangled web including numerous injury updates, tantrums, an unexpected hero, a much-maligned villain, and last-minute drama. And as painful as the defeat was, this match played a key role in the evolution of Graham’s Arsenal.
An Achilles tendon injury suffered by David O’Leary provided Graham with his first headache. Hoping to prove his fitness in a League match against Watford nine days before the final, O’Leary was ruled out before he set foot on the pitch. Booked in for an operation that would also rule him out of Euro 88, O’Leary’s absence would prove crucial.
“For me O'Leary is the Arsenal defence,” Luton striker Mick Harford informed the press. “He organises everything. I was delighted when I heard he wasn't playing, because he is so important to them.” The job of replacing O’Leary fell on the young shoulders of Gus Caesar, who hardly inspired confidence after his mistake gifted Watford a 1-0 win at Highbury in Arsenal’s last match before the final.
Harford, who had enjoyed a fine season and worked his way into international reckoning, promised to make Caesar’s afternoon as difficult as possible. But even with this boost, the task facing Luton looked immense, especially as their preparations for Wembley were also far from ideal.
Without a win against First Division opposition on grass for four months, it was only decent form on their artificial pitch that was keeping Luton out of danger in the league. A crushing 4-1 defeat to Second Division Reading in the Simod Cup final left manager Ray Harford “embarrassed and totally ashamed,” and FA Cup semi-final heartbreak against Wimbledon added to their woe.
Injuries were also dominating Luton’s plans as the final approached. Goalkeeper Les Sealey would be ruled out, leading to a rare appearance for Andy Dibble; Mal Donaghy was passed fit, despite only being rate 60-40 before the final; David Preece had only just made his first appearance in six months; and Ricky Hill had not played a first team match since breaking his leg on Boxing Day.
To add to Harford’s problems, Darron McDonagh would pull up in training on the eve of the final, and he also had to contend with Mark Stein storming out of the team hotel after he had been made substitute for the match. Luckily, older brother Brian was at hand to calm the situation down. “I told him he was being a bit silly. In the end he saw I was making sense.”
Stein junior would not be the only man to express his disappointment on the subject of team selection. When he discovered that he was not even in the match day squad, Arsenal midfielder Steve Williams disappeared completely. “I told him on Saturday he wasn’t playing,” Graham stated after the final. “I haven’t seen him since.” Williams would be fined, and never played for the club again.
Even though many pointed towards O’Leary’s absence as a glimmer of hope for Luton, most journalists agreed that Arsenal would be victorious on Sunday April 24. “All the pointers suggest the game might be as one-sided as a bout between the Christians and the lions,” Steve Curry wrote in the Express. “This line-up has too much strength and ability for Luton,” Johnny Giles agreed.
Arsenal looked far from favourites during the opening exchanges of a match played in glorious sunshine. Hill and Preece excelled despite concerns over their stamina, and 19-year-old Kingsley Black performed well, leading to a tug-of-war post-match between England manager Bobby Robson and his Northern Ireland counterpart Billy Bingham.
Luton took the lead after 13 minutes, a deft touch from Steve Foster resulting in Brian Stein ghosting in behind a static Caesar to fire beyond John Lukic. Just like 1987, Arsenal would have to come from behind. Nigel Winterburn would test Dibble from long range, but as the first half drew to a close, Luton looked fairly comfortable and Arsenal had it all to do.
Indeed it would be Luton who went closest to scoring as the second half commenced. A horrendous air shot by Caesar led to Harford crossing for Stein, the striker’s header acrobatically saved by Lukic. It looked like being a turning point.
The introduction of Martin Hayes would be a key moment in the afternoon, not a sentence that many Arsenal fans would have thought possible when talking about their wide man. But “Whoops-a-daisy” made an impact that day, equalising in the 71st minute, as the whole match turned on its head. For the next ten minutes, Arsenal were simply unplayable.
Smith put Arsenal ahead just three minutes after the equaliser; Dibble tipped a Smith header on to the bar, with Hayes somehow contriving to hit the rebound back on to the post; Hayes almost made up for his miss, only for Dibble to deny him; and the keeper later thwarted Smith when the Arsenal man was through on goal.
All Dibble’s heroics looked in vain, however, as Donaghy was adjudged to have tripped David Rocastle in the box with just nine minutes remaining. “When the penalty came I thought we were dead and buried,” Ray Harford admitted. Strangely, Nigel Winterburn stepped forward to take the spot kick, “a curious decision,” as the great Brian Moore put it.
Winterburn did not strike his penalty with much conviction, as Dibble dived to his left to push the effort round the post. “I knew I had to save that penalty or things would be over for us,” Dibble said. Arsenal’s bubble was about to burst.
Just a couple of minutes later, Caesar chose an inopportune time to dally over a clearance in his own area, resulting in a scrambled goal from Danny Wilson. The Arsenal defender would never live the moment down. Justified or not, his name is now forever linked to this match, his mistake seen as the reason why Luton went on to win the cup.
There was still time for one final act. A delicious cross with the outside of his left foot by Ashley Grimes allowed Brian Stein to sneak ahead of Tony Adams, and sink the knife into the hearts of all Arsenal supporters. There was no time for a comeback. For the first time in their 102-year history, Luton had claimed a major honour.
Man of the match and Luton hero Dibble understandably enjoyed his time in the spotlight. But he immediately cast doubt upon his future at the club, claiming that he needed regular first team football. By the summer, both Dibble and Brian Stein had left the club. However, the pair had given Luton supporters the ideal parting gift.
For Arsenal there may have been disappointment. Yet even in defeat there were some positives to be taken. The spell of football that they had hit Luton with indicated that the future was bright, and with a few additions and adjustments, Graham was able to mould together a side capable of competing with Liverpool.
But all the glory that day was Luton’s. Celebrating with a civic reception on the Tuesday night, the trophy had to be returned to Littlewoods for some repairs, the base attached to the trophy by sticky tape and a scarf. The cup was not the only damaged goods to come out of that final. Just ask Gus Caesar.