David Bentley

At various stages of his career, former England footballer David Bentley was described as ‘a great talent with a big future’ and, albeit rather optimistically, as the ‘new David Beckham’. However, in a career dogged by a serious gambling addiction and a perceived lack of commitment, particularly as far as the England national team was concerned, Bentley never really fulfilled his potential for club or country. He did win seven senior international caps for England in 2007 and 2008, finishing on the winning side five times, but started just once, in a friendly against Switzerland at Wembley Stadium in February, 2008. In June, 2014, Bentley tearfully announced his retirement from professional football live on Sky Sports, admitting that he ‘fallen out of love with the game’.

Predominantly a right-sided midfielder, Bentley made his one and only Premier League appearance for Arsenal in a 1-1 draw against Portsmouth at Fratton Park in May, 2004. He spent the 2004/05 season on loan at Norwich City, who were relegated from the Premier League on the final day of the season, and the start of 2005/06 season on loan at Blackburn Rovers. After a successful loan spell at Ewood Park, Bentley signed permanently for Blackburn Rovers in January, 2006. He made an immediate impact, scoring a hat-trick in a 4-3 home victory over Manchester United in February, 2006 and went on to score 13 goals in 88 appearances for Blackburn Rovers.

In July, 2008, by which time his England career was nigh on over, Bentley signed for Tottenham Hotspur. He scored just twice in 42 appearances for his new club, but his most memorable contribution was a spectacular, dipping volley from 43 yards in a 4-4 against Arsenal at the Emirates Stadium in October, 2008. From 2011 onwards, Bentley spent time on loan at Birmingham City, West Ham United, FC Rostov – in the Russian Premier League – and Blackburn Rovers, again, before being released by Tottenham Hotspur in 2013.

Lee Sharpe

Born and bred in Halesowen, West Midlands, Lee Sharpe was just 16 years old when he made his professional debut for Torquay United, in Football League Division Four, but made just 14 appearances for the Seagulls inthe 1987/88 season. He quickly attracted the attention of Manchester United manager Alex Ferguson and duly joined the Red Devils, for £185,000, in June, 2008.

Unsurprisingly, Sharpe took some time to adjust to life at Old Trafford, but was named PFA Young Player of the Year in 1990/91 and, in an eight-year period, would go on to make 264 appearances in all competitions for Manchester United. He won the Premier League three times, the FA Cup twice, and the League Cup and Cup Winners’ Cup once apiece, so to label him a ‘nearly man’ may appear, at first glance, unfair.

However, a personality clash with Ferguson – whom Sharpe described as ‘a very scary man at the best of times’ – not to mention a liking for the celebrity lifestyle off the field, led to ‘a few run-ins’ over the years and ultimately led to his sale to Leeds United in 1996. To be fair to Sharpe, injuries and illness did not help his cause and he was shuffled down the pecking order behind Ryan Giggs, David Beckham and Denis Irwin but, at the age of 25, his Manchester United career was over. His subsequent career, with Leeds United, Bradford, Portsmouth and, finally, Icelandic club Grindavik, was an anti-climax.

Aged 17 years and 256 days, Sharpe had the distinction of being the youngest player to play for the England Under-21 national team, but he made just eight full appearances for England; the last of them came in a World Cup qualifying match against the Netherlands in Rotterdam in October, 1993

Red Cadeaux

Red Cadeaux was a popular racehorse who was retired from racing, as a nine-year-old, after fracturing a fetlock in the Melbourne Cup at Flemington Racecourse in Melbourne, Victoria in November, 2015. Initially, the injury, while serious, was not thought to be life-threatening, but Red Cadeaux suffered ‘irreversible’ complications following surgery and was humanely euthanised later the same month.

Owned by high-profile Hong Kong solicitor Ronald Arculli and trained, in Newmarket, by Ed Dunlop, Red Cadeaux contested 54 races, worldwide, between April, 2009 and November, 2015. He won seven times, including once at the highest, Group 1 level – in the Hong Kong Vase at Sha Tin in December, 2012 – and amassed just shy of £5 million in prize money. Dunlop described the death of Red Cadeaux as his ‘saddest day in racing’.

In happier times, Red Cadeaux may have earned himself a ‘nearly man’ tag, but also developed a cult following in Australia, having run in the Melbourne Cup five years running and finished runner-up on three separate occasions. Red Cadeaux first contested ‘the race that stops a nation’ as a five-year-old in 2011 and, although sent off a largely unconsidered 30/1 chance, led inside the final furlong and failed by a rallying head to beat the French-trained Dunaden.

After a creditable eighth, from a wide draw, in 2012, Red Cadeaux tried again in 2013. Once again, he defied odds of 60/1 by taking the lead inside the final quarter of a mile and just losing out, by three-quarters of a length, in a ding-dong battle with the locally-trained favourite, Fiorente. Back again in 2014, Red Cadeaux was readily outpaced by the German-trained Protectionist in the closing stages, but nonetheless filled the runner-up berth for the third and final time, collecting nearly £484,000 in prize money for his trouble.

Ken Rosewall

Australian Kenneth ‘Ken’ Rosewall was a force majeure in men’s tennis, amateur and professional, for 25 years in the second half of the twentieth century. A short, slightly-built individual, he was sarcastically nicknamed ‘Muscles’, but was renowned for his agility and speed, which saw him win 18 Grand Slam titles, including eight in men’s singles.

Indeed, Rosewall won the Australian Open four times, in 1953, 1955, 1971 and 1972, the French Open twice, in 1953 and 1968, and the US Open twice, in 1956 and 1970. However, he never won Wimbledon, despite reaching the final on four occasions. On the first occasion, in 1954, he was beaten 11-13, 6-4, 2-6, 7-9 by Jaroslav Drobný and on the second, in 1956, he was beaten 2-6, 6-4, 5-7, 4-6 by his compatriot, and doubles partner, Lew Hoad.

Later in 1956, Rosewall signed a professional contract with promoter Jack Kramer, meaning that he was stripped of membership of the All England Club and forbidden from playing in any of the Grand Slam tournaments. Consequently, he did not play at Wimbledon again until the arrival of the ‘Open Era’ in 1968, when he was beaten in straight sets by compatriot Tony Roche in the fourth round.

Rosewall did reach the men’s singles final at Wimbledon twice more, though; in 1970, he was beaten in five sets by another compatriot, John Newcombe and, in 1974 – 20 years after his first appearance in the final – he was beaten in straight sets by Jimmy Connors who, at 21, was 18 years his junior. Remarkably, later that year, Rosewall also reached the final of the US Open, but was again brushed aside by Connors, who won 6-1, 6-0, 6-1 in under an hour.