In July, 2007, former England centre-back Jonathan Woodgate was voted the worst signing of the twenty-first century by readers of Spanish sports newspaper Diario Marca, or Marca, for short. Despite nursing a torn thigh muscle, which caused him to miss Euro 2004, Woodgate passed a medical examination at Real Madrid in August, 2004, and joined Los Blancos on a four-year contract for a fee of £13.4 million. Woodgate had been described by Newcastle United manager Bobby Robson as the ‘best central defender in England’ but, in truth, his best days were already behind him.

Woodgate’s arrival in the Spanish capital was greeted with complete astonishment and, to make matters worse, injury prevented him making his debut for Real Madrid until September, 2005. When he did, in a La Liga match against Athletic Bilbao at the Bernabeu, he scored an own goal with a diving header after 25 minutes and was sent off after 66 minutes. All told, Woodgate made just 14 appearances for Real Madrid before joining Middlesbrough, initially on loan in 2006 and permanently, for a fee of £7 million, the following year. Woodgate subsequently played for Tottenham Hotspur, Stoke and Middlesbrough, again, before retiring in 2006, but never hit the heights that seemed likely early in his career.

A graduate from the Leeds United academy, Woodgate broke into the Whites’ first team in 1997 and quickly established himself as one of the best central defenders in the Premier League. However, he failed to win any silverware with Leeds and his career at Elland Road came to an end when financial constraints forced his sale to Newwcastle United for £9 million in 2003.

Internationally, Woodgate made a total of eight, sporadic appearances for the England national team, under Kevin Keegan, Sven-Göran Eriksson, Steve McLaren and Fabio Capello, between 1999 and 2008, but a succession of injuries and an incident in Leeds town centre in January, 2000, which led to a conviction for affray, limited his opportunities.

Wait a minute, I hear you say. Are you seriously suggesting that Jack Nicklaus, arguably the greatest golfer of all time, underachieved in any way, shape, or form? The short answer to that question is no, not really, but Nicklaus’ name is included here not solely for devilment.

What you may not know is that, while ‘The Golden Bear’ won a record 18 major championships during his career, three more than his nearest pursuer, Tiger Woods, he also finished runner-up in 19 more. Nicklaus turned professional in 1961 and, the following June, recorded the first of 117 professional victories, in the 1962 US Open at Oakmont Country Club in Oakmont, Pennsylvania. On that occasion, he beat Arnold Palmer by three strokes in an 18-hole playoff.

However, although still only 22, Nicklaus was playing in his sixth US Open, having already finished second, two strokes behind Palmer, while still an amateur in 1960. Nicklaus would win the US Open again in 1967, 1972 and 1980, but also finished second in 1968, 1971 and 1982. In the Masters Tournament, which he won a record six times between 1963 and 1986, Nicklaus finished tied second three times, in 1964, 1971 and 1981, and second on his own in 1977. Likewise, Nicklaus won the Open Championship three times in 1966, 1970 and 1978, but was second, outright or tied, on six other occasions. It was a similar story in the PGA Championship, which he won five times between 1963 and 1980, but also outright and tied second twice apiece.

All told, in his career as a whole, Nicklaus contested 164 major championships – including an unbroken sequence of 154 between 1957 and 1998 – and his record of 18 wins is unlikely to be beaten any time soon. Granted the narrow margins by which major championships can be won and lost, future generations of golfers can thank their lucky stars that Nicklaus didn’t win more than he did!

Raymond ‘The Eternal Second’ Poulidor was a French professional cyclist who competed in every Tour de France between 1962 and 1976, with the exception of 1971, and failed to finish just twice, in 1968 and 1975. As his nickname suggests, Poulidor finished second three times and third five times, but never won; in fact, in his 14 attempts, he never once wore the as leader of the general individual classification.

Reflecting on his lack of success, which, he admitted was symptomatic of his lack of ambition, Poulidor said, ‘I thought what was happening to me was already marvellous enough.’ He was similarly philosophical about his ‘underdog’ status, saying, ‘The more unlucky I was, the more the public liked me and the more money I earned.’

In defence of Poulidor, his career did coincide, at various stages, with that of two other legendary cyclists, in the form of countryman Jacques Anquetil and Belgian Eddy Merckx, who won the Tour de France ten times between them. Indeed, it was Anquetil who beat Polidour into third place in 1962 and second place in 1964, while Merckx beat him into third place in 1969 and 1972.

Poulidor may have been a ‘nearly man’ as far as the Tour de France was concerned, but enjoyed a long, illustrious career, during which he won plenty of high-profile races elsewhere. In 1964, he won the general classification in the Vuelta a España or Tour of Spain and, on home soil, won the Critérium International – which was, at the time, effectively the French national championship – five times, in 1964, 1966, 1968, 1971 and 1972.

In October, 2021, former England international Kieron Dyer revealed that he had been diagnosed with a liver condition known as primary sclerosing cholangitis and required a liver transplant. While not wishing to kick the man while he’s down, it would be fair to say that, as far as his playing career was concerned, Dyer is probably best remembered for a bizarre, off-the-ball incident involving Newcastle United team-mate Lee Bowyer at St. James’ Park in April, 2005.

Already trailing 3-0, and down to ten men, against Aston Villa, Newcastle’s dreadful afternoon took a turn for the worse when Dyer apparently told Bowyer, ‘The reason I don’t pass to you is because you’re sh*t, basically’. Bowyer responded by setting about his team-mate, who responded in kind, and both players were dismissed, leaving Newcastle with just eight men for the remainder of the match.

Born in Ipswich in December, 1978, Dyer made a name for himself at his hometown club, Ipswich Town, before joining Newcastle United, for a fee of £6 million, in 1999. Under manager Bobby Robson, who took over at St. James’ Park in September that year, he was instrumental in Newcastle United finishing in the top five in the Premier League in three seasons running between 2001/02 and 2003/04. Thereafter, Dyer suffered a variety of long-term injuries, which restricted him to fewer than 50 league appearances, for West Ham United, Ipswich Town, Queens Park Rangers and Middlesbrough, in the last six years of his career. All told, Dyer made 33 appearances for the England national team. He made the 2002 World Cup squad, but made just three appearances, all as subsitute, and played just seven minutes at Euro 2004.