1) Herbert Burgess, Sandy Turnbull and Jimmy Bannister: Manchester City to Manchester United (1906)

Chelsea’s alleged hijack of Pedro’s supposed move to Manchester United might be the most recent high-profile example of wily cunning and chicanery in the transfer market, but it is certainly not without precedent. One of the more amusing examples of the practice dates as far back as the turn of the last century, but in this instance it was United who were the beneficiaries.

Formerly known as Newton Heath, United were one of several clubs under investigation by the Football Association for making illegal payments to players at northern clubs disgruntled at being paid the minimum wage: £4 during the season, reduced to just half that in the summer months. Although no evidence of skulduggery was uncovered in the United accounts, their neighbours Manchester City were not so lucky. The FA’s Consultative Committee discovered that, as well as topping up player wages with under-the-table payments, City had also been behaving with impropriety in the transfer market. In May 1906, 17 of the club’s players were suspended for six months and banned from lining up for City ever again.

With so much talent to get rid of, the club notified their rivals that they planned to sell them all at an auction to be held at Manchester’s Queen’s Hotel in December 1906. On the evening of the auction, there were no shortage of officials and managers from other clubs present, but unbeknown to them, Manchester United’s manager had pulled off a rather devious coup.

Having arrived at the venue early with a trio of targets in mind, Ernest Mangnall had secretly set up shop in an adjacent room to the lounge in which the auction was due to be staged. There, he finalised deals for the registration of City’s three best players, who he had spent the previous week tapping up: left-back Herbert Burgess, inside left Sandy Turnball and inside right Jimmy Bannister, stealing the trio from under the noses of their many other admirers before they’d been given the chance to bid for their services.

Burgess, Turnball and Bannister made an immediate impact, helping United win their first league title in 1908, in only their second season in the first division. The following campaign was less fruitful, although they did win the FA Cup. The crafty Mangnall would later resign from Manchester United in 1912 to manage another club over eight seasons during 12 war-interrupted years. He didn’t enjoy the same success at Manchester City, although in terms of legacy he is believed to have sourced their famous old former home at Maine Road.

2) Roy Keane: Nottingham Forest to Manchester United (1993)

“Roy, it’s Alex Ferguson here. Have you signed any forms?” Having shaken hands with Kenny Dalglish on an agreement to join free-spending Blackburn Rovers from Nottingham Forest for a British record fee of £4m in the summer of 1993, Roy Keane was enjoying a weekend with his kith and kin at the family homestead in Cork when he took that call.

Kenny Dalglish was insisting I honour a deal I hadn’t signed. The same Kenny Dalglish who spent months tapping me up Roy Keane

Despite knowing in his heart of hearts that he wished to join United, the Irishman told Ferguson he had given his word to Dalglish and suggested it would be dishonourable to back out of a deal that would already have been done and dusted if the Ewood Park office staff had worked just a little later before going home the previous Friday afternoon. Unperturbed, Ferguson persuaded Keane to at least travel to Manchester for a chat before putting pen to paper for Rovers.

The following Monday, instead of signing for Blackburn, as agreed, the midfielder met with Ferguson. The Scot persuaded him that United would dominate the domestic game with or without him, but would almost certainly win the European Cup with Keane on board. “It was a persuasive argument,” wrote Keane in his autobiography. “He was pushing at an open door.”

His mind made up, Keane then tackled the onerous task of phoning Dalglish to inform him of his decision. “He went crazy,” wrote Keane, before detailing a couple of spectacular expletive-ridden rants he admits bothered his conscience less and less with the utterance of each new threat and profanity. “Here was Kenny Dalglish insisting I honour a deal I hadn’t signed,” he recalled. “The same Kenny Dalglish who’d spent months tapping me up behind Brian Clough’s back.”

With Forest having been relegated from the top flight after a 16-year stay, Clough had retired as manager and been replaced by Frank Clark. Despite public statements to the contrary, Clark was resigned to losing Keane but was determined to get the best price possible for the player. United, however, were offering £1m less than Blackburn and a stalemate ensued. Following a holiday in Cyprus, Keane returned for pre-season at Forest, where he was exiled to train with the reserves.

United upped their bid to £3.5m and after two weeks in which “Rebel Roy” was unfairly criticised for his selfishness in various media quarters, Forest finally accepted a new and improved bid of £3.75m. For his part, Keane eventually accepted an offer of wages worth £1,000 less per week than those on offer at Ewood Park. The deal completed, Manchester United promptly unveiled Blackburn’s man.

A snip at £3.75m. Photograph: Murdo MacLeod for the Guardian

3) Dave Mackay: Tottenham Hotspur to Derby County (1968)

No feature on hijackings would be complete without a deal masterminded by the late Brian Clough, who employed some decidedly unorthodox methods in his tenacious dealings in the market. During his early days at second division Derby County, Clough famously convinced the Tranmere defender Roy McFarland to sign for him after travelling to his house late on a Saturday night.

Once there, he explained the benefits of the move to McFarland’s parents before getting them to rouse the player, who was asleep in bed and, by his own account, “dressed like a convict” in striped pyjamas. After some dithering, McFarland reluctantly signed the form put in front of him and later confessed to Clough that it was a decision he immediately regretted. At the time, he could have had no idea of the unlikely success he would enjoy under Clough at the Baseball Ground.

Having brought McFarland in, Clough reluctantly decided to turn his attention to Tottenham Hotspur’s double-winning superstar Dave Mackay, travelling to London on the advice of his assistant Peter Taylor despite feeling he didn’t have a hope of persuading the Scottish international to join this “humdrum, dilapidated, down in the dumps club”. Arriving at White Hart Lane, Clough was left waiting to see Mackay, who replied to his offer in no uncertain terms. “There’s no chance,” he said. “I’m going back to Hearts tomorrow, to be assistant manager. That’s it.”

Mackay was a lifelong Hearts fan who had captained the club when they won the title so impressively in 1957-58 and once declared that his sole ambition in life, since realised, had been to play for the Edinburgh club and Scotland. Clough appeared to have his work cut out persuading the 34-year-old to abandon his plan to return to the club he loved so much and join a ramshackle and provincial second division club instead.

Mackay’s head was turned by the offer of a £14,000 signing on fee (negotiated down from £15,000 by the irascible Clough), to be spread over a three-year contract in addition to his wages. He agreed to abandon his plan to return to Hearts and Clough promptly returned to Derby to inform Taylor of the good news. “I don’t believe it,” said his assistant, according to Clough’s autobiography. “I never thought you had a prayer.”

Clough would reinvent the ageing, but still classy, Mackay as a sweeper and later described him as “the most effective signing in my entire managerial career”. The Scot left the club after 122 appearances to go to Swindon Town, just one year before Derby won their first English league title in 1972.

Dave Mackay in action for Derby County against Coventry in the 1969-70 season. Photograph: Colorspor/Rex

4) Maurice Johnston: Nantes to Rangers (1989)

Outside observers could be excused for thinking little is required to cause uproar in Scottish football circles, but the unveiling of Maurice “Mo” Johnston from Nantes to Rangers in 1989 seems to be the daddy of all JFK moments. Although certainly not the first Catholic to pull on the blue shirt of Rangers (it is believed there were as many as 15 in their 117-year history before him), he was certainly the most high profile, having moved from Celtic to Nantes against his will two years previously. “I didn’t want to leave Celtic and I don’t intend to now,” said Johnston, posing in a Celtic shirt upon his apparent return to the club for a then Scottish record fee of £1.2m. “There was some rubbish about me wanting to join Manchester United but it never entered my head to play for any other club. In fact, there is no other British club I could play for apart from Celtic.” That was in May and within two months he had inked a deal with Celtic’s hated rivals, Rangers: the most British club of them all.

Johnston has never spoken at length about the change of heart that caused such a seismic reaction in Scotland and confusion remains over what exactly happened to scupper his return to Celtic. Some reports suggest the deal was stymied by a problem regarding Celtic’s failure to pay the required tax, while Johnston’s agent, Bill McMurdo, has always insisted the player wasn’t in fact Nantes’ to sell because he owned Johnston’s contract at the time. “It would only have happened if someone at Celtic had spoken to me in depth and they didn’t want to do that,” he explained.

With the uncertainty over Johnston’s future at Celtic growing, the Rangers manager Graeme Souness made his move in the hope that as well as scoring goals for his new team, the coup in stealing the best Scottish striker available from Parkhead “would damage [Celtic] for a number of years”. He wasn’t wrong. Despite the anger of many Rangers fans at the signing, Johnston went some way towards appeasing them with 31 goals in 76 league starts and was part of a team that would go on to complete a run of nine consecutive league titles after he left for Everton. Opinions differ on just how reluctant furious Rangers fans were to accept him into the Ibrox fold, but despite initial threats and media coverage of burning scarves outside the ground, their season ticket sales and average attendance was not affected. Unsurprisingly, Celtic fans were not quite so quick to forgive the treachery of their wayward Bhoy.

Glasgow Rangers manager Graeme Souness after signing Maurice Johnston. Photograph: PA/PA Archive/Press Association Ima

5) Alfredo Di Stéfano: Millonarios to Real Madrid (1953)

Having become a star at River Plate before a 1949 players’ strike in Argentina took him to Millonarios in a breakaway Colombian league that was unsanctioned by Fifa, Alfredo Di Stéfano’s registration remained in the hands of his old club while he led his new team to three titles in four years. In the dog house with River and disillusioned with life in Colombia, Di Stéfano did a runner back to Buenos Aires where he was stuck in limbo and unable to play for anyone. Fed up with what he saw as the injustice of it all, he decided to retire.

On an earlier tour of Europe with Millonarios, the Blond Arrow had caught the eye of both Real Madrid and Barcelona and it was the latter who offered him a career lifeline that he agreed to grab. In the scramble to secure his services, Real Madrid got involved, anxious to exact revenge for Barcelona stealing the Hungarian forward László Kubala out from under their noses two years previously. The curmudgeonly and refreshingly frank Di Stéfano would later write in his memoirs that “I didn’t care if I played for Barcelona or for Madrid; it was all the same to me, I just wanted to play.”

In May 1953, Di Stéfano arrived in Spain and began training with Barcelona, despite not actually having signed for them. A Fifa ruling over the Colombian bootleg league meant that his registration would not revert to River Plate for another 16 months. Barcelona had already agreed a fee with the Argentinian club, but needed to negotiate another one with Millonarios to see the deal over the line and make the problem of his registration go away. Possibly through arrogance or poor negotiating skills, having turned down several opportunities to pay Millonarios a fairly reasonable asking price, Barcelona were furious to learn Real Madrid had stepped in unbeknownst to them and agreed a deal with them instead.

What followed was arguably the most acrimonious and fractious transfer saga in the history of football, a row between two rival clubs that would help shape the future of Spanish and European football and remains a savage bone of contention between representatives and supporters of the two clubs involved to this day. It was a political tug-of-war – Franco’s regime on one side and Catalan nationalists on the other – that is chronicled in great and fascinating detail in our own Sid Lowe’s splendid Fear And Loathing In La Liga. Ultimately, it was won by Real Madrid and constitutes what is unquestionably Barcelona’s greatest ever defeat.

In a nutshell, in the face of an apparently unresolvable stalemate, Fifa were invited to adjudicate on the situation. Invoking the wisdom of Solomon, they arrived at the ludicrous compromise that Di Stéfano, who was restricted to playing in friendlies and exhibitions while getting thoroughly fed up with the behaviour of both clubs, should alternate between Real and Barcelona a season at a time for four years, at which point both clubs would reach an agreement on his future. Having asked for intervention, Real and Barça had no choice but to accept this daft compromise, but soon after Di Stéfano arrived in Madrid to begin the first season of his preposterous arrangement, Barcelona agreed to give up their claim.

Alfredo Di Stéfano on the charge for Real Madrid in 1962. Photograph: Files/EPA

Di Stéfano would go on to lead Real to eight Spanish titles (including their first for 28 years) and five consecutive European Cups, laying the foundations of a new football dynasty and sparking a revolution in the continental order. His first step on this journey of 10,000 miles was to score his first two goals for Real. They came in a match against Barcelona, who will not have been best pleased.

6) Park Chu-young: Monaco to Arsenal (2011)

Once the up-and-coming poster boy for South Korean football, Park Chu-young is probably one of those Arsène Wenger signings that might have Gary Neville pontificating at his most exasperated, presuming he has heard of the striker and can remember who he is. Having become the subject of mass national hysteria in his native country after his goals helped South Korea to victory in the 2004 Asian Football Confederations Youth Championships, the youngster signed for FC Seoul, where he enjoyed a successful three-year spell, before heading for Europe where he also did OK during three injury-interrupted seasons at Monaco that ended with their 2011 relegation to Ligue 2. It was 2011 and the club agreed that the player could leave the club.

Monaco agreed a fee of £2.7m with Lille for the player, who travelled to the north of France to conduct his medical. Halfway through it, he mysteriously disappeared from his hotel room, whereupon it emerged he had got the Eurostar to London to sign for Arsenal instead. It later emerged that the Gunners had sneakily outbid Lille and promised to better the £40,000 per week wages they were offering the 26-year-old. “We haven’t had a telephone call, nothing,” said Lille’s president Michel Seydoux in the meantime. “From what we understand he could be at Arsenal. Like Monaco, Lille are baffled. Everything had been agreed.”

While it seems Monaco may not have been as baffled about Park’s whereabouts as they claimed, Seydoux and Lille certainly seem to have dodged a decidedly expensive bullet. Park would go on to play seven minutes of Premier League football during his three years on the Arsenal payroll and is now back enjoying prodigal son status in his native Seoul.