Unsettled in Italy, Henry transferred from Juventus on 3 August 1999 to Arsenal for an estimated fee of £11 million, reuniting with his former manager Arsène Wenger. It was at Arsenal that Henry made his name as a world-class footballer and although his transfer was not without controversy, Wenger was convinced he was worth the transfer fee. Brought in as a replacement for fellow French forward Nicolas Anelka, Henry was immediately moulded into a striker by Wenger, a move that would pay rich dividends in years to come. However, doubts were raised about his ability to adapt to the quick and physical English game when he failed to score in his first eight games. After several difficult months in England, Henry even conceded that he had to "be re-taught everything about the art of striking”. These doubts were dispelled when he ended his first season at Arsenal with an impressive goal tally of 26. Arsenal finished second in the Premier League behind Manchester United, and lost in the UEFA Cup Final against Turkish club Galatasaray.
Coming off the back of a victorious UEFA Euro 2000 campaign with the national team, Henry was ready to make an impact in the 2000–01 season. Despite recording fewer goals and assists than his first season, Henry's second season with Arsenal proved to be a breakthrough, as he became the club's top goalscorer. Armed with one of the league's best attacks, Arsenal finished runner-up to perennial rivals Manchester United in the Premier League. The team also reached the final of the FA Cup, losing 2–1 to Liverpool. Henry remained frustrated, however, by the fact that he had yet to help the club win honours, and frequently expressed his desire to establish Arsenal as a powerhouse.
Success finally arrived during the 2001–02 season. Arsenal finished seven points above Liverpool to win the Premier League title, and defeated Chelsea 2–0 in the FA Cup Final. Henry became the league's top goalscorer and netted 32 goals in all competitions as he led Arsenal to a double and his first silverware with the club. There was much expectation that Henry would replicate his club form for France during the 2002 FIFA World Cup, but the defending champions suffered a shock exit at the group stage.
2002–03 proved to be another productive season for Henry, as he scored 32 goals in all competitions while contributing 23 assists—remarkable returns for a striker. In doing so, he led Arsenal to another FA Cup triumph (where he was man-of-the-match in the Final), although Arsenal failed to retain their Premier League title. Throughout the season, he competed with Manchester United's Ruud van Nistelrooy for the league scoring title, but the Dutchman edged Henry to the Golden Boot by a single goal. Nonetheless, Henry was named both the PFA Players' Player of the Year and FWA Footballer of the Year. His rising status as one of the world's best footballers was affirmed when he emerged runner-up for the 2003 FIFA World Player of the Year award.
Entering the 2003–04 season, Arsenal were determined to reclaim the Premier League crown. Henry was again instrumental in Arsenal's exceptionally successful campaign; together with the likes of Dennis Bergkamp, Patrick Vieira, Freddie Ljungberg and Robert Pirès, Henry ensured that the Gunners became the first team in more than a century to go through the entire domestic league season unbeaten, claiming the league title in the process. Apart from being named for the second year running as the PFA Players' Player of the Year and FWA Footballer of the Year, Henry emerged once again as the runner-up for 2004 FIFA World Player of the Year award. With 39 goals scored in all competitions, the Frenchman led the league in goals scored and won the European Golden Boot. However, as was the case in 2002, Henry was unable to lead the national side to honours during UEFA Euro 2004).
This dip in success was compounded when Arsenal failed again to secure back-to-back league titles when they lost out to Chelsea in the 2004–05 season, although Arsenal did win the FA Cup (the Final of which Henry missed through injury). Henry maintained his reputation as one of Europe's most feared strikers as he led the league in scoring, and with 31 goals in all competitions), he was the co-recipient (with Diego Forlán) of the European Golden Boot, and is currently the only player to have officially won the award twice in a row (Ally McCoist also had two Golden Boots in a row, but both were deemed unofficial). The unexpected departure of Arsenal's captain Patrick Vieira in the 2005 close season led to Henry being awarded club captaincy, a role which many felt was not naturally suited for him; the captaincy is more commonly given to defenders or midfielders, who are better-placed on the pitch to read the game. Along with being chief goalscorer, he was responsible for leading a very young team which had yet to gel fully.
The 2005–06 season proved to be one of remarkable personal achievements for Henry. On 17 October 2005, Henry became the club's top goalscorer of all time; two goals against Sparta Prague in the Champions League meant he broke Ian Wright's record of 185 goals. On 1 February 2006, he scored a goal against West Ham United, bringing his league goal tally up to 151, breaking Arsenal legend Cliff Bastin's league goals record. Henry scored his 100th league goal at Highbury, a feat unparalleled in the history of the club, and a unique achievement in the Premier League, On the final day of the Premier League season, Henry scored a hat-trick against Wigan Athletic in the last ever match played at Highbury. He completed the season as the league's top goalscorer, was voted the FWA Footballer of the Year for the third time in his career, and was selected in the FIFA World XI.
Nevertheless, Arsenal failed to win the Premier League title again, but hopes of a trophy were revived when Arsenal reached the 2006 UEFA Champions League Final. The Gunners eventually lost 2–1 to Barcelona, and Arsenal's inability to win the league title for two consecutive seasons combined with the relative inexperience of the Arsenal squad caused much speculation that Henry would leave for another club. However, he declared his love for the club and accepted a four-year contract, and said he would stay at Arsenal for life. Arsenal vice-chairman David Dein later claimed the club had turned down two bids of £50 million from Spanish clubs for Henry before the signing of the new contract. Had the transfer materialised, it would have surpassed the then-world record £47 million paid for Zinedine Zidane.
Henry's 2006–07 season was marred by injuries. Although he scored 10 goals in 17 domestic appearances for Arsenal, Henry's season was cut short in February. Having missed games due to hamstring, foot, and back problems, he was deemed fit enough to come on as a late substitute against PSV in a Champions League match, but began limping shortly after coming on. Scans the next day revealed that he would need at least three months to heal from new groin and stomach injuries, missing the rest of the 2006–07 season. Wenger attributed Henry's injuries to a protracted 2005–06 campaign, and reiterated that Henry was keen on staying with the Gunners to rebuild for the 2007–08 season.
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