On the night of October 16, 1957, Middlesbrough and local rivals Sunderland played a friendly to commemorate the first floodlit game to be played at Ayresome Park, England.

Cheered on by 27,000 home fans, Middlesbrough striker Brian Clough was running in on goal, looking to shoot, but a Sunderland defender took him down. As he hit the turf, the referee blew for a penalty and pointed to the spot.

For the first time under the floodlights’ glare, Middlesbrough’s right winger and expert penalty-taker, the Jamaican-born fans’ favourite, stepped forward. Lindy Delapenha took the ball and placed it on the spot.

All eyes were on him as he took a few steps back, ran up and blasted the ball past Sunderland keeper Ron Routledge before he could even move. Lindy kicked the ball so hard that it burst through the bottom corner of the net, emerging from behind the goal making it appear as if he’d missed.

As Delapenha turned away to celebrate and the referee looked to give the goal, Sunderland midfielder and future Boro manager Stan Anderson grabbed the ball and placed it on the ground for a goal kick. Upon hesitating, appeals from the Sunderland players and disbelief from the home team, Billingham referee Kevin Howley consulted his linesman and was swayed. A goal kick was given. Delapenha shook his head in disbelief as he walked away.

Lindy Delapenha had just scored the “goal that never was”.

Born in 1927 as Lloyd Lindbergh Delapenha in Kingston, Jamaica and known by many as a pioneer, Delapenha was the first Jamaican footballer to play in the English game.

After failing to knuckle down at school, the mischievous youngster was sent to boarding school, where he excelled in all sports, including cricket and athletics. Lindy placed in every event he entered, but football was his passion. After turning down the chance to become a professional cricketer, he set his sights on playing football in England. Spotted playing at school by a sports master, Delapenha was given a letter of recommendation to take to Arsenal for a trial.

The 18-year-old had yet to complete his national service, but he booked a ticket for a 14-day boat voyage from Jamaica to England on a prisoner-of-war ship containing Japanese soldiers. After arriving in Southampton, he made his way to London, where he impressed his hosts at his trial. Lindy claimed it went well, but Arsenal did not offer him a contract.

Lindy decided to join the Physical Training Corps. He was later stationed in North Africa with the Royal Fusiliers. There, he again excelled at sports and represented the army in a number of different events including running, boxing, cricket and even exhibition diving.

After turning down a chance to represent Great Britain at the 1948 London Olympics, Delaphenha was spotted playing for the army. After completing his national service and returning to England, Lindy travelled to Portsmouth for a trial. He performed well, and was signed on at half-time.

Delapenha was with Portsmouth when they won back-to-back league titles 1948-49 and 1949-50 – the most successful period in the club’s history. Still, Delapenha struggled to break in to Pompey’s greatest-ever side, which contained more experienced players, and he endured an injury-plagued two seasons at Fratton Park. He was restricted to just seven appearances and scored just one goal. After not making enough starts in his first season, Delapenha picked up a medal after his second for the games he played for the championship-winning side. He was the first black player to do so.

By chance, one of those games was against Middlesbrough – a 5-1 victory for Pompey at Ayresome Park. Delapenha must have impressed, since Middlesbrough later extended a £12,000 offer. Delapenha became a Boro player in April 1950.

Luckily for Boro, just before leaving Portsmouth, Delapenha had an operation to remove a blood clot from his thigh. After that, his injury problems seemed to cease all together. In Delapenha’s first full season with Middlesbrough, he helped them reach 6th place in the 1950-51 First Division. He made 41 appearances and scored eight goals.

During this period, Boro’s team managed to contain England internationals Wilf Mannion and George Hardwick, along with the popular Italian Rolando Ugolini in goal.

Wearing the Number 7 shirt, Lindy became a regular on the Boro side for nine seasons and was the club’s leading scorer for three seasons: 1951-52 (17), 1953-54 (18) and 1955-56 (18) all while playing right wing.

Boro’s own future World Cup-winning coach, Harold Shepherdson, who coached Lindy, said the Boro star “possessed a lethal right foot in keeping with his very fine athletic physique… I can still remember his style of play, with fierce shots from 25 to 30 yards outside the box which would crash into the back of the net.”

At 5′ 7”, Delapenha was strong on the ball, had power and pace and one of the strongest shots around. He also had a great relationship with the Boro fans, who really took to the Jamaican.

After relieving Wilf Mannion of penalty-taking duties during his second season, Delaphena became known as the “spot-kick king”. He rarely missed, and he hit those old laced-up leather balls so hard and fast they would slam into the back of the net before the hapless keeper could budge.

Although Delapenha had been playing some of the best football of his career, by the end of the 1953-54 season Boro were heading for relegation. The legendary Hardwick had left the club to player-manager Oldham Athletic. Mannion was at war with the club and wanted a transfer. Delapenha finished as the top scorer, with 18 goals, but Boro finished 21st and were relegated. “Golden Boy” Mannion headed to Hull City.

At around this time, Manchester City offered Middlesbrough £26,000 for Lindy Delapenha’s signature. At the time, the highest-ever transfer price stood at £34,500, so Manchester had made a serious offer for the winger. Lindy thought about it, but was reluctant to leave his fiancée, a local school teacher named Joan Crawford. He declined the offer from the first-division club and opted to stay at Ayresome Park. This endeared him to the Boro faithful even more.

The 1955-56 season saw the emergence of a new, locally born goal sensation, Brian Clough, who later described Delapenha as a “marvellous player” and “one of the best I have ever played with”.

With Delapenha helping to supply the crosses and through balls, Clough scored 85 goals in just under three seasons. Lindy undoubtedly set up a fair number of opportunities for Clough to score. With local boy Alan Peacock in attack and Peter Taylor in goal, Delapenha helped Boro achieve 6th– and 7th-placed finishes, but was unable to win promotion back to the first division, even with Clough scoring 40 and 42 goals in Lindy’s final two seasons.

Clough also remembered that Delapenha was the only Boro player to own a car at the time. It was a battered maroon Ford Anglia, and Lindy would give players lifts home, strictly in order of age. This meant that Clough usually ended up catching the bus. But, Clough recalls one happy afternoon Lindy drove him and his future wife, Barbra, to H Samuel Jewellers in Stockton to buy an engagement ring.

In April 1958, after an injury-plagued season for Boro, Delapenha played his last game, a 3-2 defeat at home to Blackburn. Two months later, he left for Mansfield Town, where he went on to make 115 appearances and score 27 goals over two years. There, too, he endeared himself to local supporters and became a firm fan favourite. He is still warmly remembered.

Burton Albion was the 37-year-old Delapenha’s last English club. He was a Southern League Cup winner in 1964 and scored the winning goal in the final.

After finally heading home to Jamaica, Lindy took Boys’ Town FC from the third division to the first, and ended his playing career at Real Mona. He was in his early forties.

Upon finally hanging up his boots, Lindy Delapenha forged a new career for himself in broadcasting and became a legendary sports commentator for the Jamaica Broadcasting Corporation and a director of sports for Jamaican television.

Lindy Delapenha will go down as a pioneering Jamaican footballer, a Jamaican sporting legend and, to a small group on the south coast, a cult hero who played for a first-division title-winning side.

For Boro fans, Delaphena will live on in folklore as a fan favourite who played some brilliant football alongside some of the club’s greatest. He was Middlesbrough’s first foreign import to come and dazzle the Ayresome Park crowd.

Looking back, Middlesbrough were fortunate to have Delapenha for nine seasons. Anybody who was lucky enough to see him play for the Boro will remember what a tremendous player he was.

As scorer of 93 goals in 270 appearances between 1950 and 1958 and a three-time top scorer, Lindy Delapenha was the club’s first great Number 7 and a Boro Legend who won’t be forgotten.

Editor’s Note: The above article on Lindy Delapenha was taken from the Football Fly, an English publication. It was published approximately 10 years ago.