As a player, coach and manager, Terry Venables possessed one of the sharpest football brains of his generation. His career reached its peak when he guided England to the semi-finals of the European championships on home ground in the summer of 1996, losing to Germany on penalties. But that was only after beating Scotland with an unforgettable goal from Paul Gascoigne, and trouncing a highly rated Netherlands team with the finest display seen from the national team since the World Cup victory 30 years earlier.

Venables, who has died aged 80, went into those matches already knowing that he would be replaced once the tournament was over, thanks to the dim view taken by some senior members of the Football Association, his employers, of his outside activities.

An interest in business had begun innocently enough when he became involved at the start of his playing days with a tailoring concern and the marketing of something called the Thingummywig, a covering for women to wear over their curlers. Both were early failures, establishing a pattern that culminated in the FA declining to extend his England contract, fearful of the publicity from his involvement in several business-related lawsuits.

He was a member of the group of footballers to enjoy the fruits of postwar prosperity and the lifting of the maximum wage. In his youth Venables had also briefly tried a career as a Sinatra-style crooner. Later he owned a nightclub. Football never seemed a big enough world to contain his energies.

As a clever inside forward, he won the League Cup with Chelsea and the FA Cup with Tottenham Hotspur, making two full England appearances to go with his schoolboy, youth and under-23 caps. As a manager he won the Second Division title with Crystal Palace and Queens Park Rangers, Spain’s La Liga and the Copa de la Liga with Barcelona, and the FA Cup with Spurs.

Through all the ups and downs he maintained the facade of the chirpy cockney with a knowing grin. His personality suited the headline writers of the tabloid newspapers, who greeted his move to Barcelona in 1984 by naming him “El Tel”.

Born in Dagenham, on the eastern fringe of London, during the second world war, he was the only child of Fred Venables, then serving as a petty officer in the Royal Navy, and his wife, Myrtle, who had grown up in Clydach Vale in the Rhondda Valley but moved to London with her parents as a teenager.

The infant Terry spent part of the war with relatives in Wales, and later had many family holidays there. When his parents took over a pub in Romford in the mid-1950s, he remained at school in Dagenham, living with his maternal grandparents, who encouraged his interest in sport.

Dagenham was a fertile breeding ground for footballers. Venables lived a few doors away from the family of Les Allen, an older boy who would play for Spurs and QPR and whose brothers and sons also became professionals. His first representative match was a 12-0 win for Dagenham under-11s against Paddington. The game became his overriding interest, and his time at Lymington secondary modern school was not marked by academic achievement.

His belief that he could make it as a footballer was confirmed when, following his appearances for England schoolboys, he was approached by four leading clubs: Spurs, West Ham, Matt Busby’s Manchester United, and Chelsea. Concluding that it would be harder to break into the formidable first teams at White Hart Lane, Upton Park and Old Trafford, he opted to join Chelsea. At 15, he signed forms giving him £5 a week, much of which went on his daily bus and train fares from one side of London to the other, two hours each way.

He made his first-team debut at the age of 17, alongside the 20-year-old goal-scoring prodigy Jimmy Greaves, another Dagenham neighbour. On £18 a week after signing a full professional contract, by 1961 he was a regular in a side now managed by Tommy Docherty, the tempestuous Scot, with the cerebral Dave Sexton as head coach. The League Cup was secured with a 3-2 aggregate win in a two-leg final against Leicester City in 1965.

The young footballer was already enjoying the night life of the West End. His friends now included the singers Adam Faith and Tommy Steele, although his own show business aspirations ended after a single appearance with the Joe Loss Band at the Hammersmith Palais. Nevertheless the glamour of that world retained its appeal and he would go on to own Scribes West, a Kensington club where the regulars included footballing friends, Fleet Street sportswriters and the gangster “Mad” Frankie Fraser.

Alf Ramsey, a Dagenham man of an earlier, more straitlaced, generation, had picked Venables for England matches against Belgium and Holland leading up to the 1966 World Cup, but there was no place for him in the final squad. Disputes with Docherty led to a move that summer to Bill Nicholson’s Spurs. He played in the 1967 FA Cup final, a 2-1 win over Chelsea, but found his enthusiasm and confidence waning.

They were rekindled in 1969 when he signed for Queens Park Rangers, accepting an offer from the club’s owner, Jim Gregory, who would become a significant influence on his life. Adopting the playmaker’s role in a team featuring the brilliant Rodney Marsh, he also began to undertake coaching duties, having acquired his FA qualifications.

When Malcolm Allison attracted him to Crystal Palace in 1974, his playing days were almost over. Soon he was coaching full-time and working with a group of promising young players who, when he took over as manager following Allison’s departure in 1976, won promotion to the First Division. As a new decade loomed, they were declared to be “the team of the 80s”, but soon after the start of the 1980-81 season, with Palace bottom of the table, Venables suddenly left to become manager of QPR.

In his three seasons back at Loftus Road he guided a team including Clive Allen, the son of his old Dagenham neighbour, to Wembley, where they lost an FA Cup final to Spurs, and to fifth place in the First Division. During his time there a revolutionary artificial grass surface replaced a notoriously poor playing surface. Venables had predicted the venture just over a decade earlier in the title of a football novel he co-wrote with the author Gordon Williams – They Used to Play on Grass (1971). The plastic surface lasted only a few seasons, but Venables was entitled to point out that it had prompted an improvement in standards of grass preparation and maintenance.

Meanwhile he had caught the eye of Barcelona, who offered him the head coach’s job in 1984. To replace Diego Maradona, who had moved to Italy, he brought in Steve Archibald, the Spurs striker.

Initially underwhelmed, the Catalan fans were won over when Archibald’s goals helped the club win a first league title for 11 years and a place in the 1986 European Cup final, which they lost to Steaua Bucharest on penalties. Recruiting Gary Lineker the following season proved a success, but results deteriorated and in September 1987 Venables was dismissed.

Two months later he was back at White Hart Lane, installed as Spurs’ manager. After buying Gascoigne from Newcastle United and bringing Lineker back from Spain, an FA Cup final win over Nottingham Forest was the high point of a six-year tenure during which he tried to take over the club and eventually fell out with a new owner, Alan Sugar, who in 1991 had promoted him to chief executive.

Less than a year after leaving Tottenham he was appointed England manager. While his increasingly tangled business affairs did not endear him to some FA staff, the football argument was in his favour. He transformed a side that, under Graham Taylor, had failed to qualify for the 1994 World Cup, developing a flexible tactical approach that made the most of Gascoigne’s virtuosity and the goalscoring prowess of Alan Shearer, and provided the brush with glory at Euro 96.

Once his hopes of carrying on to the next World Cup had been dashed, in 1997 he acquired a majority shareholding in Portsmouth, becoming chief executive but leaving the club in controversial circumstances within a year as the team sat at the bottom of the First Division. During a brief period managing Australia, his team reached the final of the 1997 Confederations Cup, in which they were beaten by Brazil.

Back in London, where a return to Crystal Palace as manager in 1998 ended in acrimony within a year as the club went into administration, Venables was given a seven-year high court ban from acting as a company director for mismanagement of four companies, including Tottenham Hotspur and Scribes West. A spell helping Bryan Robson avoid relegation at Middlesbrough was followed in 2002 by nine unhappy months managing Leeds United, several of whose best players were sold to pay off the club’s debts without his knowledge.

A sad short period in 2006-07 as adviser to Steve McClaren, an altogether less inspiring England manager, formed the coda to a long career in which the promise was often betrayed by the results, thanks perhaps to a refusal to give his whole attention to the game.

He and Williams had collaborated again on a successful series of detective novels that were turned into the Hazell series for Thames TV (1978-80), he launched a football board game and published two autobiographies, and in 2010 he recorded a version of an Elvis Presley hit, If I Can Dream, with the Royal Philharmonic Orchestra, reaching No 23 in the pop charts. His later years were spent in Penàguila, near Alicante, as the owner of a hotel and restaurant, El Tel once more.

A first marriage in 1966 to Christine McCann, a dressmaker he had known since his apprentice days at Chelsea, ended in divorce in 1984. He is survived by their two daughters, Nancy and Tracey, and by his second wife, Yvette Bazire, whom he married in 1991.

• Terence Frederick Venables, footballer, football manager and businessman, born 6 January 1943; died 25 November 2023