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Chelsea 1998-2000

Chelsea 1998-2000

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Was Chelsea on the verge of greatness before the Abramovich era?

In this episode of By Far The Greatest Team, we travel back to Stamford Bridge at the turn of the millennium, exploring a Chelsea side full of flair, ambition, and continental influence—before the billions arrived. From FA Cup glory to a European semi-final and the Premier League’s first all-foreign XI, we chart the club’s evolution during one of its most intriguing transitional periods.

Join us as we unpack Chelsea’s rise from 90s underachievers to a team with real silverware ambitions. We revisit the pivotal roles of Ken Bates, Glenn Hoddle, Ruud Gullit, and Gianluca Vialli, and examine how key players like Gianfranco Zola, Dennis Wise, Mark Hughes, and Jimmy Floyd Hasselbaink helped shape the club’s identity. Plus, we dive into the backlash, the Full Members Cup, and the cultural shift in English football that made Chelsea both admired and controversial.

How close was this side to true greatness? Tune in and find out.

Takeaways:

  • The legacy of Ken Bates and the Hoddle-Gullit-Vialli managerial transition
  • Why Chelsea’s continental approach sparked both innovation and criticism
  • The significance of the 1997 and 2000 FA Cup wins
  • How signings like Zola and Hasselbaink redefined Chelsea’s playing style
  • The strategic shift that foreshadowed the Abramovich revolution

🎧 Listen now and rank this Chelsea side’s place in football history with us.


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