1) Tom Finney (Preston North End and England)

The end of the 1952-53 season is remembered for the Matthews Final, as Stanley finally picked up the winners' medal his rich talents deserved. But 24 hours before the match, another of England's undecorated post-war heroes was cruelly denied a prize. Preston North End – star man Tom Finney – had won their last three games of the league campaign, and sat two points clear on top of the First Division. Arsenal had to win their game in hand, at home to Burnley on the Friday night before Blackpool and Bolton contested the FA Cup final, to deny Preston on goal average. They did, going a goal down, hitting back with three quickfire strikes, then letting one in during a nervy second half before the final whistle blew. Arsenal won 3-2 and pipped Preston by 0.099 of a goal.

Finney would never come so close to a medal again. He would come close enough, mind, when 12 months on from the moment of Matthews's crowning glory, the nation hoped Finney could provide another emotional narrative at the 1954 FA Cup final.

Matthews apart, Finney had been English football's biggest star in the decade after the resumption of football. A one-club man, he was only ever interested in playing for Preston – which was just as well, given that the board effectively told him he could whistle for a move when Palermo came calling in 1952, wafting a £10,000 signing-on fee under his nose. But an FA Cup winners' medal with his hometown club would be something of a consolation for a man forced to supplement his basic football wage with a midweek plumbing job.

Preston were, rather unfairly, known to some wags as "the pPlumber and his 10 drips". They were far from a one-man team – Charlie Wayman and Tommy Docherty were also in the side – but it was all about Finney, who according to Donny Davies (the Guardian's "Old International") had "an ability so extraordinary that it has been said that whoever has Finney on his side should win any match".

The problem for Preston was that their 1954 FA Cup final opponents were West Bromwich Albion. Vic Buckingham's side were pretty purists, and had just been pipped to the league title by the much more direct Wolverhampton Wanderers. They had been "crippled", according to Davies, by "injuries, anxieties and a loss of form". Having just fallen short in the first leg of an unprecedented 20th-century Double, they were in no mood to throw away the second prize either.

Also, Finney, though he was keeping it quiet, was carrying an injury. He failed to perform in the final – his signature game would have to remain England's 4-0 drubbing of Italy in 1948 – and it would be Albion's outside right, Frank Griffin, who scored a fine individual late winner, controlling a cross from the right with his head to wrongfoot the North End backline, then adroitly guiding a shot across the keeper into the bottom-left corner.

So another classic last-gasp victory in the final, but no Matthewsesque denouement for England's hero. Preston came second in the league once again in 1957-58, but there was a five-point gap between the Lilywhites and winners Wolves that year. Finney would have to make do with his status as one of world football's all-time greats, a wildly popular hero in Preston and England to this day. Not such a bad consolation, given that neither money nor medals can buy you love. But a Finney Final would have been nice, wouldn't it?

2) Len Shackleton (Bradford Park Avenue, Newcastle United, Sunderland and England)

At least Finney had a big day out to remember. Nothing so grand for the great inside forward of the immediate post-war years, Len Shackleton, who as a result is predominantly remembered for his Clown Prince image: that empty director-baiting page in his autobiography; anecdotes of teasing international managers for yuks ("Which side of the net do you want me to put it in, Mr Winterbottom?"); tales of hanging around in opposing penalty boxes with the ball at his feet, pretending to check his watch and comb his hair.

In many ways Shacks was 20 years ahead of his time; he would have been right at home as one of the 1970s mavericks. Not least because the likes of Stan Bowles, Tony Currie and Frank Worthington won nothing either. Shackleton's career boils down to a few choice moments, both good and bad: six goals on his debut for Newcastle, including a hat-trick in 155 seconds; a bizarre attempt at an overhead clearance in thick fog which led to the winner for Yeovil in the 1949 FA Cup, as Sunderland became the victims of perhaps the biggest giantkilling ever; a goal against the newly crowned world champions West Germany in his last international in 1954.

His big near miss came in 1949-50, when Sunderland were by some distance the leading goalscorers in the First Division, and topped the table going into Easter. But Sunderland stumbled, allowing Portsmouth and Wolves to nip ahead. Going into the final day, Sunderland trailed their two rivals by a point. They won their last game of the season, against Chelsea, 4-1, but both Pompey and Wolves won too. Portsmouth won their second title on the bounce.

Shackleton's Sunderland reached the 1954-55 FA Cup semis, only to lose to Manchester City. Interestingly, for a player painted as something of an eccentric showboater, it was not for the want of Shackleton trying. "It is impossible for Shackleton to take part in any Association Football function win which his original approach to the matter in hand and his superb technique fail to make their impress," wrote our Old International. "Cool and imperturbable as always, Shackleton was soon extracting involuntary Oos and Ahs of wonderment or trepidation from the rapt crowd as he flicked the ball up in the air with one foot before lobbing it neatly and precisely to its destination with the other." His promptings "turned the last tumultuous half-hour into an ordeal" for City, who nevertheless held out. Shackleton's personal roll of honour would remain as blank as that famous page from his book.

3) Johnny Haynes (Fulham and England)

There was plenty of talent at Craven Cottage in the 50s and 60s – Johnny Haynes, George Cohen, Bobby Robson, Jimmy Hill (yes) – but none of these big names won any domestic prizes. We don't have to feel sorry for Cohen, who won the biggest prize of all with England. Robson would go on to be a managerial success story with Ipswich Town, England, PSV Eindhoven and Barcelona. And Hill, of course, reinvented football first on the pitch, with his firebrand trade unionism, and then on screen by inventing punditry.

Haynes, however, won nothing with England. He won his last cap as captain at the 1962 World Cup, where his displays were generally poor. ("A genuine class act, a fine passer of the ball," opines Cris Freddi in the Complete Book of the World Cup. "But not against World Cup defences.") He did not manage. And his sole legacy to football was to famously break the £100-a-week wage barrier, though much good it did him. (The Fulham chairman Tommy Trinder had publicly claimed he'd happily pay Haynes such money, the sort of fee he'd get for treading the boards at the Palladium, only his hands were tied by the minimum wage. When it was lifted, Trinder had no choice but to pay it. "I give him credit, he stood by it," said Haynes years later, "but the only thing wrong was that everybody in the country knew what I was getting. I played for Fulham for another eight years, and I never got a rise. It always stayed at £100.")

He was also not going to win any major prizes at a relatively small club such as Fulham. He did have chances to leave for clubs who regularly hoovered up trophies – Internazionale bid for him in 1961, while Tottenham Hotspur wanted him to fill the late John White's boots in 1964 – but both times he opted to stay at Craven Cottage. As a result, the nearest he came to glory was the 1958 FA Cup semi-final, when second-division Fulham took a post-Munich Manchester United to a replay. Haynes (along with Hill) was one of the stars of a 2-2 draw, but despite also being one of the star performers in the rematch, United were too strong and won 5-3. (An aside: the replay, played at Highbury, was United's first match in London since Munich. The game before they flew to Belgrade ahead of the disaster was also at Highbury – and ended 5-4 to United.)

Haynes never gathered a medal to match his talents. After retiring from Fulham in 1970, aged 35, he did win a title in his dotage for Durban City, in the ever-so-slightly-dodgy whites-only South African National Football League. A medal we're not counting for so many different reasons.

4) Joe Baker (Hibernian, Torino, Arsenal, Nottingham Forest, Sunderland, Raith Rovers and England)

Joe Baker broke into the Hibernian team in 1957 as a 17-year-old, and was soon making headlines when Hibs visited their Edinburgh rivals in the Scottish Cup. Baker scored all of his side's goals in a 4-3 win; this against a Hearts side who were on their way to winning the league by 13 points with a goal difference of +103. Hibs made it to the final, where they lost 1-0 to Clyde. It would be the closest Baker ever got to a medal.

He began to rattle the goals in from all angles, scoring 42 in 33 games in 1959-60, by which time he had become the first England international with a thick Scottish accent. (He was born in Liverpool, but brought up by his Scottish parents in Motherwell.) During the following season, he scored nine goals in a 15-1 Scottish Cup win over Peebles Rovers. Naturally, as a fated nearly man, he missed a penalty in that game. But he soon earned himself a £70,000 transfer to Italy. Both Fiorentina and Torino bid for him; he chose the latter, heading abroad with Denis Law.

Baker played well in Turin, where he again quickly showed his liking for local derbies, scoring a winner against Juventus. But events off the pitch took over – he crashed his car, ending up under the emergency surgeon's knife; punched a press photographer into a canal, and went on hunger strike upon falling out with the club management – and he was soon back in Blighty with Arsenal.

Baker scored at a rate of two goals every three games at Highbury, but Billy Wright's team were going nowhere. Baker was sacrificed, offloaded to Nottingham Forest in early 1966. He continued to score regularly, but couldn't force his way into England's World Cup squad. The following season, Baker scored 16 league goals as Forest finished runners-up behind Manchester United. Like the Hibees' cup run nine years earlier, it was close but no cigar. A spell at Sunderland saw only relegation. Baker ended his career back home in Scotland, with Hibs and then, his last move, to Raith. Hibs won the 1972 Scottish League Cup not long after he left.

5) Clive Allen (Queens Park Rangers, Arsenal, Crystal Palace, Tottenham Hotspur, Bordeaux, Manchester City, Chelsea, West Ham United, Millwall, Carlisle United and England)

The very thought of Coventry City must make Clive Allen feel a little queasy. In 1980, playing for Crystal Palace against City at Highfield Road, he belted a free-kick into the top-right corner of the goal, then wheeled away to celebrate a spectacular strike. The problem for him was Coventry were pootling upfield, the cheeky buggers, playing on as though nothing had happened, the ball having ricocheted from the in-goal frame and back on to the pitch. "It hit the stanchion!" a ringleted Allen could be clearly seen mouthing, under the circumstances showing remarkable restraint by not using the words eff, cee, and effing cee. Innocent times.

Six seasons later, he again faced Coventry, this time as a Tottenham Hotspur player at Wembley in the 1987 FA Cup final, and again he would have absolutely no luck. After two minutes of the match, Allen scored by converting a right-wing Chris Waddle cross with a near-post header that was both deft and powerful, a flash of brilliance that would surely see hot-favourites Spurs on their way to victory over unfancied opponents. But of course Coventry came back to win a superlative final with one of the great Wembley displays. And what's worse, Allen's magnificent header was upstaged by Keith Houchen's famous dive, obscured utterly by some once-in-a-lifetime brilliance.

Allen had scored 49 goals in the season, but – Spurs having also faltered badly in a league tussle with Everton, and somehow conspired to snatch defeat from victory's slavering maw against Arsenal in the semi-finals of the Littlewoods Cup – had nothing tangible to show for them, bar a record nobody in England has come close to matching since. The following year saw Allen leave for Bordeaux, who had recently won leagues and cups but were on the downturn. He returned to England with Manchester City, before stints at Chelsea, West Ham and Millwall brought him another record: the most London clubs joined by any one player in history: seven. No hard metal on the end of a ribbon for that, either, of course.

6) Matthew Le Tissier (Southampton and England)

Our final player: decisions, decisions. Terry Paine or Matthew Le Tissier? Both played for Southampton, both won absolutely nothing during their careers, and both are fine examples of why medals in the grand scheme of things mean bugger all.

Paine spent 18 years at Southampton, rattling up 713 appearances, before joining Hereford United for a further 111. Those 824 games were a league record for an outfield player until 1999 (he was overtaken by Tony Ford) while his shift at The Dell remains a club record.

Le Tissier enjoyed a 16-year stint at Saints, spent largely wandering around conserving energy, while occasionally wafting an insouciant boot at a ball which would invariably screech along an aesthetically pleasing and often mathematically dubious arc towards the net. He scored the last goal in a competitive match at The Dell in May 2001, a last-minute juggle of comic-book preposterousness. The same month – no coincidence – saw the final Roy of the Rovers strips published, Racey having been rendered totally redundant.

Neither player is unlikely to be forgotten any time soon on the south coast. By way of comparison, anybody been thinking about Paul Gilchrist, Jim Steele or Mel Blyth recently?

As Paine was retrospectively awarded a World Cup winners' medal in 2009 for partaking in a group game at the 1966 World Cup, Le Tissier must get the nod. Partly because Po' Matt's pockets are empty, but mainly because there's the very strong suspicion that Le Tissier simply does not care, having long ago sussed that medals really aren't the point.