Walter Samuel, Christian Vieri, andriy shevchenko

The 19 Biggest Football Transfers of the Summer of 1999

May 14, 2025 Rasmus Kristensen

The summer of 1999 was one of the most explosive in football transfer history. As Serie A reigned supreme and Europe’s top clubs scrambled to bolster their squads ahead of the new millennium, record-breaking deals and high-profile moves dominated the headlines. From teenage sensations to world-class strikers, the transfer window was a showcase of ambition, power, and shifting allegiances across Europe.

Here are the 19 biggest transfers of that unforgettable summer, ranked from the 19th to the most expensive move of all.

19. Roque Santa Cruz – Olimpia to Bayern Munich (£6.75m)

At just 17 years old, Paraguayan striker Roque Santa Cruz made a high-profile move from Olimpia to German giants Bayern Munich. The £6.75 million fee showed Bayern’s intent to invest in long-term attacking potential.

Read the full article

18. Marco Di Vaio – Salernitana to Parma (£7m)

After scoring goals for a struggling Salernitana side, Di Vaio was snapped up by Parma for £7 million. His pace and finishing made him one of Serie A’s most exciting young forwards.

17. Michel Salgado – Celta Vigo to Real Madrid (£7.8m)

A tireless right-back with a reputation for aggression and grit, Salgado joined Real Madrid for £7.8 million. He would go on to become a defensive stalwart during the Galáctico era.

16. Enrico Chiesa – Parma to Fiorentina (£8.5m)

Italian international Enrico Chiesa moved to Fiorentina for £8.5 million. The veteran striker was brought in to partner Gabriel Batistuta in one of Serie A’s most lethal front lines.

15. Sonny Anderson – Barcelona to Lyon (£9m)

After limited opportunities at Barcelona, Sonny Anderson transferred to Lyon for £9 million. His move would help establish the French club’s rise to domestic dominance in the early 2000s.

14. Simao Sabrosa – Sporting Lisbon to Barcelona (£9.2m)

The talented Portuguese winger joined Barcelona at age 19 in a £9.2 million move. Despite flashes of brilliance, his time at the Camp Nou would be short-lived before returning to Portugal.

13. Gianluca Zambrotta – Bari to Juventus (£10m)

Zambrotta left Bari for Juventus in a £10 million switch. The dynamic wide man would later reinvent himself as a world-class full-back and key figure in Italy’s 2006 World Cup triumph.

12. Chris Sutton – Blackburn to Chelsea (£10m)

Sutton became the most expensive English player at the time when Chelsea paid £10 million for the Blackburn striker. However, his lone season at Stamford Bridge was largely disappointing.

11. Angelo Peruzzi – Juventus to Inter (£10m)

Veteran goalkeeper Peruzzi made a £10 million move to Inter to bring stability between the posts. With experience from Juventus and the national team, he was seen as a safe pair of hands.

10. Simone Inzaghi – Piacenza to Lazio (£10m)

Filippo’s younger brother Simone earned a big move to Lazio after an impressive spell at Piacenza. The £10 million fee reflected the Rome club’s desire to strengthen their attacking options.

9. Dani – Mallorca to Barcelona (£10m)

Portuguese forward Dani moved to Barcelona for £10 million but struggled to make an impact at the Catalan club. Despite his talent, he couldn’t secure a regular place in the lineup.

8. Elvir Baljic – Fenerbahce to Real Madrid (£10m)

Bosnian international Baljic made a surprise £10 million move to Real Madrid. Although he arrived with high hopes, injuries and inconsistency marred his stint in Spain.

7. Walter Samuel – Boca Juniors to Roma (£13m)

The “Wall” arrived in Serie A when Roma paid £13 million to sign Samuel from Boca Juniors. His aggressive and composed defending made him a fan favorite in Italy.

6. Darko Kovacevic – Real Sociedad to Juventus (£14m)

Juventus paid £14 million to bring the Serbian striker back to Serie A. Known for his aerial strength and clinical finishing, Kovacevic added depth to Juve’s forward line.

5. Vincenzo Montella – Sampdoria to Roma (£15.3m)

“The Little Airplane” took flight in Rome after a £15.3 million transfer from Sampdoria. Montella’s knack for scoring made him a perfect addition to Roma’s ambitious squad.

4. Andrii Shevchenko – Dynamo Kyiv to Milan (£15.7m)

Andriy Shevchenko — ph.FAB / Shutterstock.com

One of Europe’s most anticipated transfers saw Shevchenko join Milan for £15.7 million. The Ukrainian forward would become a club legend and Ballon d’Or winner at San Siro.

3. Juan Veron – Parma to Lazio (£19m)

“Il Brujita” Veron moved to Lazio for £19 million, bringing creativity and flair to their midfield. His arrival was a statement of intent from a club looking to dominate domestically and in Europe.

2. Marcio Amoroso – Udinese to Parma (£21m)

After winning Serie A’s golden boot, Amoroso switched to Parma for £21 million. The Brazilian’s explosive pace and finishing made him one of the league’s most feared attackers.

1. Christian Vieri – Lazio to Inter (£31m)

Inter shattered the world transfer record by signing Vieri for £31 million. The Italian hitman was seen as the final piece in Inter’s quest to reclaim domestic and European glory.