The Best Premier League Transfers Ever: Thierry Henry to Arsenal (1999/2000)

Emmet Gates

• Updated: 23 May 2023 08:47 CDT
• 4 min read

Not many would’ve predicted how the signing of winger Thierry Henry from Juventus in the summer of 1999 would transform Arsenal in the new millennium, but Arsene Wenger certainly knew the untapped potential that lay within the 1998 World Cup winner.

This article is part of FootballTransfers’ greatest-ever Premier League deals. We have selected just one standout transfer from every season of the Premier League, including two honourable mentions. This list will then be gathered to provide a definitive list of the best pieces of business in the Premier League era.

Thierry Henry, Juventus to Arsenal, £10.5m

The signing of Henry almost went under the radar in the summer of 1999. Whilst the winger was signed for a vast sum in 1999 terms, only the most keen observers of the French game would’ve known a great deal about the talent Henry possessed.

The French international decided to leave Juventus after general manager Luciano Moggi wanted to send him on loan to Udinese in a deal including Brazilian striker Marcio Amoroso. Henry rejected the idea and made it known that he wanted to leave Turin after only six months.

Henry’s arrival in England wasn’t all plain-sailing. He struggled to find form in the early going, and didn’t find the back of the net until his eighth game of the season, away to Southampton. Yet after that he never looked back. The goals and assists flooded in, and so too did the trophies. A Premier League title would come in his third season at Highbury, and a second in his fifth.

Arsenal won the FA Cup twice during Henry’s stint in north London. He also reached the finals of the UEFA Cup and the Champions League, narrowly losing on both occasions.

Henry morphed from an inconsistent winger into one of the most feared strikers in Europe under Arsene Wenger. And at times was virtually unstoppable, especially during his peak years of 2002-06.

228 goals and 104 assists in 376 games in all competitions is a phenomenal return, and Henry’s transfer doesn’t just go down as one of the best of the 1999/00 season, but of all time in the Premier League.

Runners-up: Sami Hyypia, Willem II to Liverpool, £2.6m

Hyypia’s move to Liverpool was arguably the best of the eight made by the club in the summer of 1999. The Finland international signed from Dutch outfit Willem II for £2.5m and slotted straight into the heart of the Liverpool defence. Hyypia was ever-dependable and stayed at Anfield for a decade, playing over 300 games for The Reds, and winning a multitude of trophies during his stay, including the Champions League in 2005.

Runners-up: Mikael Silvestre, Inter to Manchester United, £4m

The Frenchman signed for Manchester United for £4m weeks into the start of the 1999/00 campaign. Silvestre had been a bit-part player at Inter in the previous season, but turned out to be United’s best acquisition in a season where many of their summer signings didn’t cover themselves in glory. Silvestre was remarkably flexible, and could play either at left-back or at centre-back, and featured in the majority of United’s games in the 1999/00 season. The Frenchman stayed at Old Trafford for nine years, winning multiple league titles, and also the Champions League in his final season at the club.