English clubs splashed out Stg£348 million in the transfer market during 1999, taking the spending in the 1990s beyond Stg£1.8 billion.
Transfer fees are still heading for the sky despite the Bosman ruling, which many thought would signal the end of the transfer system.
Last year's figure was six times more than the annual expenditure in 1990, although Bosman changes mean "invisible" fees are also being paid to players and agents.
Premiership clubs were responsible for the lion's share of the spending.
Liverpool topped the 1999 charts, splashing out £28.7 million on new players, but Treble winners Manchester United found themselves in the bottom half of the Premiership spending table for the last 12 months.
Liverpool clawed back £14.7 million for players sold in 1999, but lost £14 million on transfers during the year. The deficit would have been much less if Steve McManaman had not left for free.
The Bosman ruling has served to distort the figures. Manchester United spent £11 million on transfers during 1999 but will also have coughed up a considerable amount to lure free agent Mark Bosnich to Old Trafford and to hang on to Roy Keane.
Arsenal, who made a transfer profit largely thanks to the sale of Nicolas Anelka for £23.5 million, Leeds and Newcastle all spent more than £20 million.
Wimbledon also broke into the transfer big league in 1999 spending £16.5 million.