An exceptional dribbler on the wing also capable of playing as an attacking midfielder and as a second striker, he is often regarded within the media as "Australia's finest football export", despite his career being blighted with injury. Against Croatia he scored the crucial goal to get Australia through to the knockout stages of the 2006 World Cup. He is a member of the Executive Committee of the Australian Professional Footballers' Association.
During his time at Westfields Sports High School, Kewell played at representative level for both school and club competitions. He played in the New South Wales Youth League representative team, and for the Marconi Soccer club from U13 to U15.
He was sent off in Leeds United-Galatasaray UEFA Cup 1999-00 semi-final match. Playing mostly in a left midfield role and in attack, Kewell became one of Leeds' young stars in a troop of highly promising youngsters, eventually playing alongside fellow Australian Mark Viduka. The high point of this period was when they helped Leeds to the semi-final of the UEFA Champions League in 2000-01. However, the club began to suffer financial difficulties and, by 2002-03, having sold many of their best players, Kewell and Viduka's efforts in front of goal merely prevented Leeds' slide from being relegated from the Premiership. Kewell's efforts at Leeds United gained him international recognition for his talents as the finest left footer in the game at the time. He scored 45 goals in over 130 appearances for Leeds over eight years.
Kewell left Leeds under acrimonious circumstances. In an infamous interview given to the BBC shortly before his move to Liverpool, Kewell lashed out against the staff at the club, stating that the medical staff worsened his injuries and that his teammates had ostracized him.
Kewell's transfer was highly controversial because it was alleged that a significant portion (£2m of the £5m) went to Kewell's unregistered agent, Bernie Mandic to ensure that he ended up at Anfield. In a related matter, Kewell sued Gary Lineker in 2005 for defamation of character, but, with the jury unable to agree on a verdict, the parties had to settle out of court.
On 25 May 2005, Kewell became the only Australian-born player (Craig Johnston was born in South Africa) to win the UEFA Champions League, playing in Liverpool's win over A.C. Milan on penalties. Kewell was controversially selected by Benítez ahead of the defensive midfielder Dietmar Hamann, signalling the club's intent to attack from the outset. The gamble proved unsuccessful, and an injured Kewell was substituted early in the first half with a torn adductor muscle. Liverpool were losing 1-0 at the time and Kewell was infamously booed off the pitch by Liverpool fans with many suggesting he had faked the injury. It also emerged during the summer of 2005 that Kewell had been playing throughout the season with an undiagnosed sports hernia, also known as 'Gilmore's Groin.'
In November 2005, after recovering from the injury sustained during the final, Kewell spoke to the Liverpool FC official website, saying that he had a strong desire to repay his manager Rafael Benitez for showing confidence in him by fielding him in the Champions League Final. He also thanked his wife and friends for the support shown to him while he recovered from injury. He also re-stated the severity of the injury which had forced him off in the Final and told his doubters that they were misguided to question the severity of his injury.
Kewell's form for Liverpool in the 2005-06 English Premier League season showed what he was truly capable of, scoring goals and plenty of assists, lending support to his assertion that his prior mediocre performance was the result of poor health rather than apathy. Kewell scored his first league goal at Anfield in over 2 years when Liverpool beat Spurs 1-0 in January, he was also the only scorer when Liverpool beat Man City 1-0 at Anfield and scored the last goal in a 3-1 win over Everton in one of his best displays of the season. Kewell was also one of Liverpool's best performers in the FA Cup semi final win over Chelsea which Liverpool won 2-1.
Kewell played in the 2005-06 FA Cup Final, only to be substituted in the 48th minute due to abdominal pains (the supporters reaction this time was more sympathetic compared to the previous years champions league final). It was later confirmed by Liverpool that he had torn a groin muscle, but was expected to be fit for the World Cup.
On April 30, 2007 Kewell made his comeback from almost a year out of club football. He came on as a 55th minute substitute for Liverpool F.C. Reserves in a 'mini-derby' against Everton F.C. Reserves. On May 5, 2007, he came on as a substitute in the second half of Liverpool's match against Fulham at Craven Cottage, having not played for Liverpool since his substition in 2005-06 FA Cup Final. On May 13th 2007, Harry came on as substitute in the second half against Charlton in the last game of the Premiership. Speculation on whether he was to be selected in Liverpool's upcoming Champions League Final in Athens rapidly became positive for Kewell after providing an excellent game against Charlton. Harry provided a cross in for Dirk Kuyt to assist towards a Xabi Alonso goal and then scored a penalty on the 90th minute. He played in the Champions league Final in Athens, coming on as a second half substitute for Bolo Zenden.
Kewell was injured for the start of the 2007-08 season, and he faced an uncertain future at Liverpool having suffered yet another injury, which has sidelined him for the first month of the Premier League season. Kewell returned as a substitute in Liverpool's Carling Cup victory over Cardiff City F.C. on October 31, coming on in the 71st minute. He has since come on as a substitute in the Premier League and UEFA Champions League against Blackburn and Besiktas respectively. After his return Liverpool manager Rafael Benitez stated on the club's website and to other members of the media that a new contract for Harry to continue his career at Anfield was not out of the question. Many believed that if Kewell could stay injury free until the seasons end he would be offered the chance to remain with the club.
Kewell found himself unable to make the team after Liverpool's Carling Cup defeat to Barnsley. Benitez revealed that Kewell was training extra with the reserves in a bid to win a new contract. .
His chances of a new contract were hindered however, when seeking games and match fitness, he travelled with his national team to play in a game against Singapore. Kewell returned to England with a groin strain, unfortuntely leaving less time to prove himself worthy of a new deal.
His first goal of the 2007-2008 season was for the Liverpool reserve team in their 2-0 win over rivals Manchester United. Because of injuries, his future at Liverpool was uncertain During the January transfer window, he was linked with a move to Fulham F.C..
In May 2008 it was revealed Kewell had turned down a new contract at Liverpool.
On 5 July 2008, Turkish champions Galatasaray signed Kewell to a two-year deal. He said ''"I wanted to move on and this is the best way. I can't wait to get started, it's just what I'm looking forward to, a new challenge."
Kewell's transfer to Galatasaray provoked strong criticism from fans of his former team Leeds United as he was a Leeds player when two of their fans were killed in clashes before a UEFA Cup semi-final against Galatasaray in Istanbul in April 2000. Kewell responded and in an open letter he stated "I chose the No 19 shirt when I signed for Galatasaray AS as a sign of respect for Leeds because that was the number I got when I first became a regular member of the Leeds United FC starting XI. "I felt that it might be a way to demonstrate that I had not forgotten where it all started and I was hoping that in a small way it would help the healing process of the tragedy that occurred on the 5th of April 2000. To blame the Galatasaray AS club for the tragedy in Istanbul is simply wrong and discriminatory." This letter failed to help him and he is now held in very ill regard by Leeds fans.
Kewell made his debut for Galatasaray in the Turkish Super Cup where he came on as a substitute after 66 minutes, scoring his first goal for Galatasaray in the 2-1 win over Kayserispor. He also provided the assist leading to the second goal. He scored his second goal for Galatasaray in the first league match of the season against Denizlispor, with Galatasaray going on to win 4-1. He has scored 5 brilliant goals in 8 competitive matches for Galatasaray, 3 of which were in the Turkish league, showing that despite his long bout with injury, his natural ability and skill still remain.
Kewell became the youngest player to début for the Australia national team when he played against Chile in April 1996, aged 17 years and 7 months. In November 1997, Kewell was selected to play for Australia in the country's World Cup qualifying game against Iran. At the Azadi Stadium in Tehran, in front of an estimated crowd of 100,000, Kewell scored his first ever goal for his country and gave Australia a 1-0 lead. Iran eventually drew level and the game resulted in a 1-1 draw, which set up a tense return game in Melbourne.
A then-record crowd for Australian football of 85,000 - at the Melbourne Cricket Ground - witnessed the second leg of this World Cup qualifier against Iran, as well as Kewell's second goal. The Socceroos eventually stretched their lead to two goals but Iran fought back and scored two vital away goals to finish the game 2-2 and qualify for the 1998 World Cup in France.
In November 2005, Australia qualified for the 2006 FIFA World Cup taking place in Germany. It was the first time Australia had qualified for the World Cup since 1974 when it was held in West Germany. To reach the World Cup Australia beat Uruguay in a two-legged play-off. Kewell was considered instrumental in the Socceroos' defeat of Uruguay, turning the course of the match when he entered as a substitute. He scored the first penalty for Australia in the deciding penalty shoot-out, which they went on to win 4-2.
Kewell played in Australia's opening game of the 2006 FIFA World Cup against Japan in Germany. He did not start for Australia in their second group match against Brazil but again entered as a substitute, missing an early opportunity when Dida punched the ball out dangerously. Kewell was reported to FIFA by referee Markus Merk for verbal abuse after the match but he escaped being sanctioned.
In the Croatia vs Australia game Kewell scored Australia's second goal to equal the score at 2-2. Australia only needed a draw to qualify for the second round for the first time. He was also awarded Man of the Match, which made him Australia's second Man of the Match at a World Cup after Tim Cahill who had won an award earlier in the tournament. Even though he was obviously not fully fit in the World Cup he still proved to be a big match player when Australia needed him.
Due to suspected gout, (later diagnosed as septic arthritis — a bacterial infection in the joints of his left foot) Kewell was unable to play against Italy in the knockout stage, which saw Australia eliminated from the World Cup.
Kewell did not play for the national team for a year following the World Cup, and made his national-team comeback in a friendly against Singapore in late June 2007. The match was Australia's last before the Asian Cup and Kewell came on as a substitute in the 65th minute, and went on to score his eighth international goal and provide a cross for the final goal in a 3-0 victory. Kewell was a key part of the Australian squad for the Asian Cup. Kewell scored his 9th international goal for Australia, scoring the 4th goal in a 4-0 victory over Thailand in the Asian Cup. After the group stage, in a quarter-final against Japan, Kewell was sent on to the pitch to replace Mark Viduka in the 61st minute, in a 1-1 draw. A penalty shootout was required to break the deadlock and Kewell's first penalty shot for Australia was stopped. Australia ultimately lost the shootout and was eliminated from the Asian Cup.
Kewell did not play either of Australia's first two matches against Qatar and China. Kewell was made captain for Australia's qualifier against Iraq at Suncorp Stadium on June 1, 2008. He scored the only goal with a header in the 47th minute as Australia won 1-0. Kewell also scored the third goal against Qatar in Australia's 3-1 win to put them into the final qualification round. In a world cup qualifier warm up game against the Dutch, he scored a penalty won by Joshua Kennedy. Australia went on to win 2-1 with Harry Kewell playing a vital part for the national team in the first half.
As of May 2008, Kewell has become the face of Australian men's fashion brand, Politix.