5 of Arsenal's best transfer windows of all-time

#2 Summer 1999

Thierry Henry could go down as Arsenal's greatest ever player

Arsenal might’ve lost one of the biggest stars of the 1997/98 title-winning campaign in the summer of 1999 when they sold sulky French striker Nicolas Anelka to Real Madrid, but at least they received some serious money for him - £23.5 million – and with some of that money at least, they bought a replacement who turned out to be his superior in all ways, basically, a man who went on to become one of the Gunners’ all-time legends and their record goalscorer.

That man was, of course, Thierry Henry, who broke the record that Ian Wright had worked so hard to achieve in just six years. And while he couldn’t lead them to the Premier League title instantly, he did finish as the club’s top goalscorer in his maiden season with 26 in all competitions.

Two seasons later, he scored 32 as Arsenal won the league and then 2003/04 saw him net 39, as Arsenal won the league and went the whole season unbeaten – the ‘Invincibles’ season.

Overall, in 7 of his 8 seasons at Arsenal, Henry finished as their top goalscorer, and he also hit over 30 goals in five of those seasons too. Sure, other 1999 signings such as Sylvinho (two decent seasons) and Davor Suker (way past his prime during his Arsenal run) didn’t fare as well, but who cares?

The window saw them sign probably their best ever player, which means it’s got to be ranked highly.