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Roberts scored two goals on debut, in a midlands derby against Wolverhampton Wanderers. In 2018, Roberts said still regretted not completing a hat-trick in the match, a feat he did achieve in April 1994, against local rivals Derby County. As recently as 2017, this achievement is still recalled in a chant by Leicester City fans. Roberts broke some ribs a few weeks later and returned to the first-team squad just in time for the 1993-94 play-off final, which Leicester won.

Roberts himself has ascribed his slow start to his lack of physical conditioning. Walker left the club shortly before the end of the season and was replaced during the summer by Bruce Rioch. During pre-season training, Roberts weighed in at 15 stone 3 pounds, with a body fat ratio of 16–17%, when his "fighting weight" should have been "just under 14 stone with around 13 per cent body fat." The turnaround was, according to Roberts, due to some clever psychology by Rioch:

Because of the coverage in the book, the Football Association retrospectively investigated the incident and Roberts was banned for three matches for the offence. Roberts commented that this "left "a bitter taste" – especially after England captain David Beckham escaped without a punishment for his deliberate foul in the World Cup qualifier against Wales." The Football Association said there was "insufficient evidence" to charge Beckham with bringing the game into disrepute. This was "despite his admission in The Daily Telegraph and subsequent apology." At the time, Roberts told The Daily Telegraph, "I do not want players to get suspensions and fines, but there must be consistency, regardless of who the player is." However, the book was praised by critics.

Roberts has the UEFA A Licence for football coaching and, speaking in 2007, had not ruled out getting into management. He told the Eastern Daily Press, "I've done my qualifications. It's just getting a club to give me a chance and taking it." When Norwich sacked manager Nigel Worthington, Roberts applied for the manager's job. "I tried to go for it ... knowing I wasn't going to get it but I'd never really been for an interview and I thought if I did it would stand me in good stead. But I never got a response from the club and that really disappointed me. A week after Peter Grant got the job I got a letter through the post saying 'We won't be considering you this time'. And I thought 'I've known that for the past seven days'."

Since retiring as a player, Roberts, who speaks fluent Welsh, has worked as a commentator for Sky Sports, Radio Cymru and BBC Wales. His book, All I Want for Christmas ..., a reference to his gap-toothed appearance, prompted both controversy and praise when it was published in 2004.

After being released by Norwich he joined Gillingham, there was much speculation regarding his next career move. He received a number of offers but eventually signed a two-year contract with Gillingham where he would be player/coach. It did not prove a good move for Roberts and he had a number of disagreements with the club, particularly after Stan Ternent had succeeded Andy Hessenthaler as manager. In December 2004 Roberts had himself served as joint caretaker manager, along with Darren Hare and Paul Smith, after the sudden departure of both Hessenthaler and initial caretaker John Gorman. In March 2005 he joined Cambridge United on loan until the end of the season, scoring his 200th league goal on his debut. Cambridge were relegated from League Two. In August 2005, Roberts retired from playing after reaching an agreement with Gillingham to pay the final year of his contract.

In 2004, Roberts published an account of his last season at Norwich, entitled All I want for Christmas .... The title of the book was a reference to Roberts' missing front teeth, a joking reference to the song All I Want for Christmas Is My Two Front Teeth.

A few days before the club's last home match of that 2003–04 season, Norwich manager Nigel Worthington announced that Roberts would not be offered a new contract when his deal expired that summer. Worthington felt that, following promotion to the Premiership, the club had to look to the future and that Roberts was now surplus to requirements. The Norwich supporters gave him a rapturous reception at his last match for the club at Carrow Road and during the post-match promotion celebrations Roberts wore a T-shirt that bore the legend 'Thanks for 7 great years'. With the championship already won, Worthington restored Roberts to the starting line-up for the last game of the season at Gresty Road against Crewe Alexandra and made him captain for the day. Roberts scored twice as City won 3–1. The first of his goals that day is rated by many Norwich fans as one of the best that he ever scored for the club. Overall, he scored 96 goals in 306 games for Norwich. "Iwan Roberts scored two goals, one of them an absolute corker, to bring the curtain down on a wonderful career in highly appropriate fashion."

During the 2002–03 season, Roberts captained the Norwich City team. That season, in a match against Sheffield Wednesday at Carrow Road, Roberts scored twice to move into third place on the list of Norwich City's all-time leading goalscorers, overtaking Robert Fleck in the process. The season overall, however, was not a happy one for Roberts or Norwich. The Canaries faded after a good start to the season and failed to qualify for the play-offs, while Roberts scored just 7 goals in 47 games leading many supporters to believe that his best days were behind him. The 2003–04 season would be his last at Carrow Road and although he was no longer an automatic selection for the first team he played an important part in one of the club's best-ever seasons. The team won the division one championship in style and were promoted to the premiership. Roberts weighed in with some crucial goals, including the winning goal in a top-of-the-table match against Sheffield United. Roberts revealed in his autobiography that in February of that season he had a cancer scare and had to have a malignant melanoma removed from his arm.

In 2002, Roberts was made an inaugural member of the Norwich City F.C. Hall of Fame. In 2007, Roberts came third in a vote run by the Norwich Evening News to determine which Norwich legend would be inaugurated into the Professional Footballers' Association Centenary Hall of Fame.

During that 1999–2000 campaign there was speculation about Roberts's future as his contract was due to expire in the summer of 2000. Shortly after he signed a contract extension in January of that season, Bruce Rioch left the club and was succeeded by Bryan Hamilton. Roberts helped Hamilton make a good start when he scored both goals in a 2–0 win at Portman Road against City's rivals Ipswich Town F.C. on 19 March 2000. However, Roberts and Hamilton did not have a good relationship during the Ulsterman's short spell in charge and after Hamilton left the club during the 2000–01 season, Roberts intimated that if he had known that Hamilton was going to succeed Rioch then he would not have signed his contract extension.

Although Roberts was personally enjoying the most productive spell of his career, his four years so far at Carrow Road had seen the club struggle. They had barely threatened to qualify for the end of season play-offs and in the 2000–01 campaign had struggled against relegation from Division One. The 2001–02 season – with new manager Nigel Worthington in his first full season in charge – saw the team fare better and they reached the Division One play-off final at the Millennium Stadium in Cardiff. Roberts missed much of the second half of the season because of injury, but came off the substitute's bench in the final to give Norwich the lead in the first minute of extra-time with a clinically taken headed goal. Norwich lost the match in a penalty shoot-out after Birmingham had equalised. Roberts took – and scored – the first penalty of the shoot-out but misses by Phil Mulryne and Daryl Sutch proved costly as Birmingham were promoted to the Premiership.

The book proved controversial, because it included an admission of a deliberate stamp on Wolves defender Kevin Muscat, an incident that had taken place in 2000:

Roberts worked hard on his fitness and the following season saw him finish as the club's top goalscorer with 23 goals in 51 games. Norwich fans voted him player of the season. In the 1999–2000 season he was again top scorer (19 goals in 49 games) and retained the player of the season award. He just missed out on becoming the first player in the club's history to win the award 3 years in a row when Andy Marshall finished narrowly ahead of him in the voting for the 2000–01 season.

Roberts threw himself into weight training and soon reached a target weight of 13 stone 10 pounds. "Walker had left by time the 1998–99 season got under way but his decision to spend big money on Roberts was quickly vindicated as the powerful frontman netted 23 goals in partnership with the flourishing talent of Craig Bellamy who weighed in with 19 to earn Rioch's side a place in the top half of the table."

In July 1997, Norwich City manager Mike Walker paid £850,000 to Wolves to secure the services of Roberts. His time at the club did not begin happily, however. Following his debut in August 1997, he struggled throughout the 1997–98 season and scored just 7 goals; "there were certainly those in the stands who were questioning whether he was worth the near £1,000,000 splashed out on him".

His goals and performances for Leicester persuaded Wolves to sign him for £1.3m in the summer of 1996. He spent only one season at Molineux and confirmed in his 2004 book that he did not enjoy his time there and does not have any fondness for the club, due largely to the mentality of many Wolves supporters. He did, however, score a hat-trick for the club in a match against their bitter local rivals West Bromwich Albion, (and four goals in the two games against them that season), and, overall, scored 12 goals in 33 games.

Roberts has three children, a son named Ben and twin daughters Eva and Chase (born in 1995). His charity work includes work with Norwich anti-drugs cause the Matthew Project.

In the Premier League in 1994-95, Leicester struggled and were relegated, but Roberts was top scorer. He scored another 19 goals the following season, as Leicester reached the play-off final again, but was forced to miss the final through injury. With the side promoted again, Leicester decided to sell Roberts to Wolves. In all, Roberts scored 41 goals in 100 league games for Leicester.

At Huddersfield he scored 50 goals in 142 games. In November 1993 he was signed by Leicester City. Neil Warnock, Huddersfield's manager, needed to sell players and Leciester managr Brian Little took an interest.

He scored nine goals in 63 games for the Hornets before moving to Huddersfield Town prior to the start of the 1990–91 season.

While a Watford player, Roberts was called up to play for Wales for the first time, an April 1989 friendly game against Israel. He made his debut for Wales in October of that year, in a 2–1 defeat at home against Holland in a qualifying match for the 2002 FIFA World Cup.

Roberts made his debut for the Welsh national team on 11 October 1989, when he took to the field in a 2-1 defeat to Holland in a World Cup qualifier at the Racecourse Ground, Wrexham. He went on to win a total of 15 caps for his country over the next 12 years, but never scored. He faced tight competition for a regular place in the Welsh national side for most of his career, from the likes of Ian Rush, Mark Hughes, Dean Saunders and later John Hartson.

Roberts began his professional career at Watford, when he joined as a trainee, signing his first professional contract in July 1986, shortly after his eighteenth birthday.

Roberts scored his first goal in professional football on 16 September 1986; it was the only goal in a 1–0 win against Manchester United at Vicarage Road.

Iwan Wyn Roberts (born 26 June 1968) is a Welsh former professional footballer who played as a striker from 1986 to 2005. Since retiring as a player, he has worked as a sports commentator.