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Upon retirement, Whiteside studied to become a podiatrist, graduating with a degree from the University of Salford, and served Northwich Victoria as their assistant manager/physio from October 1991 until March 1992. He quit the role as he did not enjoy the amount of time spent travelling between games. During his playing career, he had attended courses at Lilleshall to pick up his coaching badges, but he did not wish to go into coaching. He instead became an after-dinner speaker. He also worked for the Professional Footballers' Association, while taking a postgraduate course at Manchester Metropolitan University. He later took up private practice as a podiatrist in Manchester. Since 1994, he has also worked at the corporate hospitality department at Old Trafford. In 2003, he released a book entitled My Memories of Manchester United. With the help of writer Rob Bagchi, he released his autobiography entitled Determined in August 2007, published by Headline, and with a foreword by actor James Nesbitt. When Saturday Comes magazine reviewer Joyce Woolridge wrote that "Determined is an entertaining, well written account of one of the less ordinary 1980s footballers, with the added twist of how Whiteside was able to rebuild his life, if not his knee." The next month it was reported that Whiteside had been diagnosed with irregular heart rhythms. Whiteside worked as a pundit on ITV's coverage of UEFA Euro 2016.

However intense running sessions ran by coach Mick Lyons took their toll on his right knee, and on 20 September 1990 he took a knock in a practice match, which required him to have yet another operation on his right knee. After the return of Howard Kendall as manager in November 1990, Whiteside managed to appear in a few reserve team games, but this only delayed the inevitable, and he was forced to retire from the game at the age of 26 in June 1991. He had a testimonial game between Manchester United and Everton at Old Trafford in May 1992, but as United lost the title the previous week, only 7,434 turned out for the occasion.

He remained with United until July 1989, when he was sold to Everton for £600,000. However, he retired from playing two years later, aged only 26, due to a knee injury.

In view of Whiteside's medical reports, Ferguson rejected bids of £500,000 from Osasuna of Spain and from Ron Atkinson's new club Sheffield Wednesday, before accepting a bid of £600,000 (with £150,000 to follow if Whiteside reached 50 games) from Everton in July 1989. This was to the dismay of some of the club's supporters, who felt that there was still a way back for Whiteside at Old Trafford. Ferguson intended to build his own team having signed midfield duo Neil Webb and Mike Phelan, and also in the hunt for other players including Paul Ince, Gary Pallister and Danny Wallace.

Whiteside signed a four-year contract with Everton, and Alex Ferguson helped him to negotiate a pay deal that would see him earn more in two years at Goodison Park than he had done during his eight years in Manchester. He was also offered £50,000 to put his name to a tabloid article criticising Ferguson, though he declined the offer. At the time Everton boasted more recent success than Manchester United, having won two league titles, an FA Cup and the European Cup Winners' Cup. Manager Colin Harvey was planning to boost the "Toffees" chances of more silverware, and also in 1989 signed Mike Newell, Martin Keown, Stefan Rehn and Raymond Atteveld. Whiteside became Everton's playmaker in 1989–90, and formed an effective partnership with Stuart McCall in midfield to score 13 goals in his 35 appearances. Everton finished the season in sixth place, some 20 points behind rivals Liverpool.

At the start of the 1987–88 season, Whiteside represented the Football League in a game against the 'Rest of the World' to celebrate the league's centenary. He formed a solid partnership with new signing Brian McClair, scoring 10 goals in 35 appearances, though United finished second in the league behind Liverpool, and he often found himself back in midfield or on the bench when Peter Davenport was selected to play alongside McClair. However, he felt that he was due a better contract, and decided to 'call the bluff' of the club by handing in a transfer request. Recovering from injury and abuse from some supporters for his transfer request, he put what many United fans call the best performance of his career at Anfield on 4 April 1988, when he came off a substitute with his team 3–1 down to help United to salvage a point.

He ruptured his Achilles midway through the 1987–88 season and missed almost a year of first team action. Whiteside's goal in a 2–1 win over Derby County in a league match at the Baseball Ground on 10 February 1988 would prove to be his last for Manchester United.

In the summer of 1988, he was put on the transfer list and came close to joining American club Portland Timbers, before injury put negotiations on hold. A £1million price tag also deterred a great deal of potential interest.

In the summer of 1988, Ferguson brought striker Mark Hughes back to Old Trafford after two years away, further limiting Whiteside's opportunities for the first team. His continued fitness problems, and the growing competition for places in the first team, meant that Whiteside played just six league games in the 1988–89 season.

He married wife Julie on 4 October 1987; the two had met when Whiteside was 16 and she was 20. The relationship blossomed despite fears of reprisal on Shankill, with him being a Protestant and Julie being a Catholic. The marriage ended acrimoniously in 2001, after the couple had 20 years together and three children: Della, Blaine and Clodagh. He subsequently married Denise.

Then came a decline in his career at an early age, which started to around the time of the arrival of new manager Alex Ferguson in November 1986, the change of manager coming after a dismal start to the season led to the decision to sack Ron Atkinson. Whiteside, still only 21, was facing trouble from his right knee which was now beginning to require serious medical procedures to prevent it from causing his retirement. Ferguson put Whiteside back up front, and in turn he scored three times in his first four games back from injury. Ferguson did though have to rebuke Whiteside after some of his numerous drinking sessions. He ended the 1986–87 season with 10 goals in 37 appearances, however United could only manage an 11th-place finish.

Northern Ireland won qualification to the World Cup for a second successive tournament with a goalless draw with England in their final group game; Whiteside scored three goals during the qualification process, with his strike again Romania at Windsor Park proving to be crucial as they ended up qualifying at the Romanian's expense. At the 1986 FIFA World Cup finals in Mexico, he scored with a deflected free-kick in the 1–1 draw against Algeria at the Estadio Tres de Marzo. They were beaten in their other two group games, losing 2–1 to Spain and 3–0 to Brazil. Whiteside won a total of 38 caps and scored nine times in eight years playing for Northern Ireland.

By February 1985, he had started just eight games in the 1984–85 season, having fallen behind in the pecking order to Stapleton, Hughes, and new signing Alan Brazil. However, injury to midfielder Remi Moses left an opening at the centre of the field, and Whiteside proved to be a revelation in the role with his intelligent play and positioning skills, and stayed in midfield for the rest of manager Ron Atkinson's time at the club. He formed a solid partnership with Bryan Robson, despite the two being similarly attacking players, and United lost just one of their first 15 games with this new midfield partnership in operation. Whiteside scored the only hat-trick of his professional career in a 4–2 home win over West Ham United on 9 March 1985, in the FA Cup quarter-finals; it was a 'perfect hat-trick' in that he scored once with each foot and once with his head. He went on to score the winning goal in the 1985 FA Cup Final, curling a shot in from the right hand side in the 20th minute of extra time, to give ten-man United victory over Everton, and Whiteside his second FA Cup winner's medal. The goal required vision, timing, and precise shooting; and The Guardian praised his "cool footballing brain" and "clever concealment of the shot". After this success he negotiated a new contract of £60,000 a year.

United won their first 10 league games of the 1985–86 campaign, and unbeaten from their first 15, and seemed destined to win the First Division title. However they dropped off in mid-season and won just six of their final 18 games to end the season in fourth place, 12 points behind champions Liverpool. The press blamed the decline in form on the club's drinking culture and Ron Atkinson's lax disciplinary attitude, though in his autobiography Whiteside denies that this was to blame, and states that stories of the player's drinking sessions were exaggerated.

He featured in qualifying for UEFA Euro 1984. They won their final group game 1–0 over West Germany, Whiteside managing to get the better of one of the world's best man-markers in Karlheinz Förster. However the Germans secured the only qualification place in the group in their final match of the group with a late winner over Albania.

Manchester United later accepted a £1.5 million offer for Whiteside from A.C. Milan, and offered him £100,000 in cash to accept the transfer. He refused the move as he felt he still had a good future with Manchester United and because he was given only a brief time to consider whether or not to relocate to a club and location he knew little about. He continued to impress, despite on-loan striker Garth Crooks being tipped to take his first team place and sign a permanent contract (which never happened). United were trophyless however in 1983–84, exiting both domestic cup competitions to Third Division sides. He did though play a part in the 3–0 win over Barcelona at Old Trafford in the Third Round of the European Cup Winners' Cup, which overturned a 2–0 deficit from the first leg. He lost his starting place to Mark Hughes for the semi-final clash with Juventus at the Stadio Olimpico di Torino, which ended in a 2–1 defeat.

Whiteside helped Northern Ireland win the 100th and last edition of the British Home Championship in 1983–84.

Whiteside began his career at Manchester United, signing professional forms in 1982 at the age of 17 and quickly becoming a key member of the side. He scored 68 goals in 278 league and cup appearances for the club over the next seven years, picking up two FA Cup winners medals in 1983 and 1985, as well as playing in the 1982 FA Youth Cup final, the 1983 League Cup final, and the FA Charity Shield in 1983.

Whiteside holds records as the youngest player to take part in a World Cup, the youngest player to score in a League Cup and FA Cup final, and the youngest player to score a senior goal for Manchester United. Winning 38 caps for Northern Ireland, he played at the 1982 and 1986 World Cups, and also helped his country to win the last ever British Home Championship in 1983–84. After retiring as a player he became a podiatrist, and still works at the corporate hospitality department at Old Trafford.

Whiteside became United's youngest first team player since Duncan Edwards in 1953, when he made his debut as a substitute against Brighton & Hove Albion in a 1–0 league win at the Goldstone Ground on 24 April 1982, two weeks before his 17th birthday. He later played in the FA Youth Cup final defeat to Watford, though it would be just another year before he appeared in the final of the senior competition. He turned professional at Old Trafford on his 17th birthday, signing a three-year contract, and he shared a room with Steve Coppell, who was heading into retirement due to a knee injury of his own. He also struck up a close friendship with Paul McGrath, who would also face similar problems with his knee. On the final day of the season, eight days after his 17th birthday, he became the club's youngest goalscorer in a 2–0 home win over Stoke City.

His performances at the World Cup convinced manager Ron Atkinson to start Whiteside alongside Frank Stapleton at the front of United's attack for the 1982–83 season. The pair were similar players in that they held the ball up and made frequent runs into the box, allowing midfielder Bryan Robson to join in the attack. Whiteside scored four goals in the first five games of the campaign, before entering a seventeen-game drought. He scored six goals in 16 games in domestic cup competitions that season, helping Manchester United to the finals of both the League Cup and FA Cup, notably by scoring past Arsenal in the FA Cup semi-finals. At the age of 17 years and 323 days, he beat Liverpool centre-half Alan Hansen to score in the League Cup final defeat at Wembley, making him the youngest player to score in a League Cup final; his consistent performances against Liverpool during the 1980s earned him the moniker of the "Scourge of the Scousers" from United supporters. He gave an assist to Stapleton in the FA Cup Final, which finished as a 2–2 draw with Brighton & Hove Albion. At the age of 18 years and 18 days, he then scored a headed goal in the replay, which United won 4–0, to become the youngest player score in an FA Cup Final. He also became the first player to score in both domestic cup finals in the same season. He played 57 times in all competitions that season and missed just three league games, scoring a total of 14 goals.

Whiteside broke Pelé's record as the youngest player to appear in a World Cup, when he debuted for Northern Ireland aged 17 years and 41 days at the 1982 World Cup in Spain. When selected for the World Cup squad by manager Billy Bingham, he had played just two competitive games at club level. The opening game against Yugoslavia at the La Romareda in Zaragoza on 17 June was his international debut; he received a yellow card in the second half for a challenge on Nenad Stojković, and the game finished goalless. Five days later he helped his side to a 1–1 draw with Honduras, which was a disappointment, and many believed had doomed Northern Ireland's chances of advancing in the competition. They needed a win against hosts Spain in the third and final group game at the Mestalla Stadium in Valencia. They faced a partisan atmosphere with a mostly Spanish crowd and a Spanish speaking referee in Héctor Ortiz who was unwilling to punish dirty play from the Spanish players. However a mistake from goalkeeper Luis Arconada gifted Gerry Armstrong the only goal of the game, and despite having Mal Donaghy sent off on 60 minutes, Northern Ireland went on to record a 1–0 win. Whiteside played at left-midfielder for the 2–2 draw with Austria at the Vicente Calderón Stadium. A win against France would take them into the semi-finals, however a French team inspired by Michel Platini won 4–1 and therefore eliminated Northern Ireland from the competition.

His injury problems started as early as 1980, when he was 15 years old and saw Glentoran's physio Bobby McGregor to resolve a groin strain; Whiteside said that the highly physical massage he was subjected to damaged his pelvis and robbed him of his natural pace. His lack of pace was later seen as the one weakness in his game. Six weeks into his apprenticeship, in July 1981, and an innocuous looking challenge by a Preston North End player in an 'A' team game saw Whiteside requiring an operation on his right knee. Had the injury occurred a couple of years later he would have been able to have pioneering keyhole surgery, which could potentially have saved his career. After a seven-month lay-off and a further operation to remove cartilage, he returned to fitness in January 1982. He had to adapt his playing style to compensate for his damaged knee and pelvis, and developed well under youth team coach Eric Harrison.

Norman Whiteside (born 7 May 1965) is a former Northern Ireland international footballer who played in two World Cups. He played both as a midfielder and as a striker.