July 1997 saw the end of Ian Crook's 11-year Carrow Road career when the City skipper flew out to Japan to sign a lucrative one-year contract with Sanfrecce Hiroshima. He had been offered a further one-season deal with the Canaries to add to his tally of 418 senior appearances - which left him seventh on the club's all-time list - and 24 goals. However the J-League offered too many incentives and so Crook opted to join former teammate and best friend Mark Bowen in the far East rather than stay in East Anglia. The 34-year-old midfield maestro admitted: "It is an opportunity I can't turn down. It was nothing detrimental about the offer here but the money is a big, big part of it and it's a great opportunity, especially at my age." However Crook did not rule out a return to Carrow Road in the future - possibly in a coaching role. "If the gaffer fancies someone to make his tea for him in a year's time I would be interested." His new manager was Scottish boss Eddie Thomson formerly Terry Venables' predecessor as manager of the Australian national side. After his first year in Japan, he was offered another year's contract with Hiroshima. Ian himself expressed interest in the Norwich City job after Mike Walker's sacking.

Ian then moved on to Australia to play for Sydney based side Northern Spirit who were owned by Mark Goldberg, owner of Crystal Palace. Spirit were being touted as a feeder club for Palace. One of his new teammates was Robbie Slater who played for a number of English sides including Southampton, West Ham, Blackburn and Wolves. According to the Teamtalk website, Ian Crook was being lined up to join Norwich City as assistant to manager Bruce Rioch in 1999 because Director of Football Bryan Hamilton will be taking a stronger role in managing the club's football academy. Rob Newman has also been linked with this post which eventually went to Doug Livermore.

Ian initially retired from playing and concentrated on coaching at Northern Spirit. In February 2000, he was promoted to the position of Assistant Manager and has even returned from retirement to play again for the Spirit against Wollongong. "Crooky is a great player in his own right, but he is also the type of guy who lifts others around him when he is on the field," said Graham Arnold, Spirit's manager and a former teammate of Crook's from their days at San Frecce in the Japanese J-League. "I just think Crooky needs to be on the field. The players have enormous respect for him; they respond to him. With Crooky leading them they will have direction as well as thrust." (Eastern Daily Press 1st February 2000). With Crooky looking after Northern Spirit Youth who provided players for the Australian Under 17 national side that reached the final of the World Youth Championships in 1999, the hope is that Chippy will refer some of them on to Norwich in the hope that the next Mark Bosnich or Harry Kewell will be there for Norwich's benefit.

Ian was named by Teamtalk as a potential successor as Norwich City manager following Bruce Rioch's resignation on 13th March 2000. When Bryan Hamilton (Rioch's successor) resigned the following December, it was immediately alleged that Norwich directors had been in contact with Chippy to form a new management team, possibly with Mark Bowen. In May 2001 Ian was appointed head coach of Australian NSL side Newcastle United. Newcastle finished 2nd last in the just completed season and he is being seen as the man to take the club up the ladder. He is handling the media very well and making a good impression. In May 2002, he was named Australian Coach of the Year for the National League for taking Newcastle to the National Soccer League finals, a task repeated in 2003. However the 2003/4 season saw them finish third from bottom and Chippy was sacked in April 2004.

In May 2004, Ian took on possibly the worse job in international management when he took over managing the World Cup campaign of American Samoa, which FIFA ranks as 203rd among the world's 204 national A selections. The Samoans' last tilt at the World Cup saw them enter the Guinness Book of Records when they lost 31-0 to Australia. Approached by the American Samoa FA, Crook accepted an assignment the Mission Impossible bunch probably wouldn't consider, even
with bargepole in hand. He said he did so through his sense of adventure and desire to maintain a record of never having been unemployed during 24 years in professional football. It will be a tough challenge as American Samoa comprises six specks in the Pacific Ocean inhabited by merely 60,000 people. Its greatest claim to fame is as the site of the world's largest tuna cannery. Organised soccer only started in 1981 and is still played almost exclusively by college students. American Samoa has played 21 senior international matches, mainly against fellow Pacific islands minnows, and has lost them all.

At the end of November 2004, Crook was appointed Assistant Manager of Australian A-League side Sydney FC, initally under former German international Pierre Littbarski and then under former English international defender Terry Butcher who took control in the summer of 2006. Ian was linked in October 2006 with the vacancy at Carrow Road following Nigel Worthington's sacking. Poor form saw Sydney FC shareholder Anthony LaPaglia call for Butcher to be sacked and Crook to be placed in charge. This cause a break down in relations between Crook and Butcher which saw Chippy ousted from the first team's training sessions and left with the youth team. On 3rd January 2007, he quit the club to link up with his former boss Pierre Littbarski as assistant at Japan's second-division J-League outfit Avispa Fukuoka.

In October 2007, Crook and Littbarski were linked with the vacant Norwich City manager's position following the departure of Peter Grant

In the autumn of 2008, Ian applied for the manager's position at new Hyundai A-League side North Queensland Thunder FC which eventually was awarded to former Rangers midfielder Ian Ferguson. On 23rd October 2008, Ian was appointed as the high-performance manager.for the Newcastle Jets ahead of their first venture into the Asian Champions League. The new role will encompass a variety of responsibilities, but Crook's main focus will be on preparing the club's assault on the Asian Champions League next year and youth development.

On 21st January 2009, Ian returned to Norwich as first team coach as part of new manager Bryan Gunn's new management set-up. He stayed for the 2009/10 season under Paul Lambert but left the club by mutual consent in May 2010 to return to his family in Australia. He was quickly linked with a return to England with former colleague Pierre Littbarski who had applied for the vacant Carlisle and Notts County positions.

On 16th June 2010 Ian signed an two years contract as Director of Coaching for Sydney Olympic Football Club who play in the New South Wales Premier League.

Ian left Sydney Olympic in 2010 to take up the position of Head Coach at the New South Wales Institute of Sport. He then joined Sydney FC (Australian A-League) working with former player Steve Corica and under former Czech International Vitezslav Lavicka. Following the departure of Vitezslav Lavicka at the end of the 2011/2012 season, Crook was appointed manager of Sydney FC on 14th May 2012

Crook quit as Sydney manager on 11th November 2012 following a 3-2 defeat to arch rivals, Melbourne Victory. This was on the back of a humiliating 7-2 loss to the Central Coast Mariners the previous week. Crook has only be in charge for six games. He claimed the pressure of the job started to affect his health and he realised he wasn't the right man for the high-profile role.

In January 2013, Crook was appointed by Football NSW as Coach Coordinator for the Men's and Women's Premier League clubs. As well as co-ordinating with the coaches and technical directors of the senior sides, he will also assist clubs with both their Youth Development plans and overall technical direction.

Crook said “I am very grateful to have been given this opportunity by Football NSW to help engage with up and coming coaches and technical directors to further enhance their abilities to help promote the sport. Football is an ever growing sport with a healthy participation rate; the same can be said in regards to the number of up and coming coaches as well who are joining our ranks and are overseeing the development of our future players.”

In March 2014, he was linked with the Assistant Manager position at Western Sydney Wanderers FC. This became reality on 12th June 2014. He stayed with Wanderers for eight seasons in various role, finishing as Technical Director.

He left Wanderers in August 2022 to take up the role of Technical Director at second-tier side Manly United who are also based in Sydney. Manly United chief executive David Mason said he feels he has landed 'one of the best football minds in the country' after appointing the 59-year-old. 

The Early Years

Ian is up there with Steve Bruce and Dave Watson as one of the ultimate bargain signings that the club has ever made. He began his career at Tottenham Hotspur but made only 20 league appearances for them. His midfield role being blocked by the talents of Glenn Hoddle, Mickey Hazard, Steve Perryman, Ossie Ardiles, Gary Stevens etc. He left Spurs in June 1986, four years after his league debut. He cost Norwich just £80,000 and after a slow start, became a regular in the Norwich midfield. His pinpoint passing ability and technical skills especially free kicks had won him many admirers including an England B cap.

Ian will always be highly regarded by the Norwich fans even though his final season at Carrow Road was marred by his controversial signing for Ipswich Town the previous summer. At the end of the 1995/96 season, Norwich's financial difficulties led to cost-cutting exercises and Ian was granted a free transfer along with Mark Bowen and Jeremy Goss. In June 1996, he signed for arch-rivals Ipswich but his contract and player registration forms were postdated until the beginning of July. Mike Walker was re-appointed as Canaries manager on the same day that Ian was paraded as an Ipswich signing. Walker offered Crook a new contract which he duly signed. The dispute went to a tribunal and although "Chippy" Crook was able to play for the Canaries, the club was fined for its actions. Although some sections of the Carrow Road audience suspected Crook's career was on its last legs, he managed to make 37 league appearances (4 as substitute) during the 1996/97 season scoring twice (Portsmouth (A) and QPR (A) ). This brought his final tally of appearances for Norwich to 418 with 24 goals.