Hasselbaink: England’s Mistakes, Trent’s Midfield Gamble, Leeds & Chelsea Career | Stick to Football EP 92
Stick to Football
The Overlap
4.6 • 686 Ratings
🗓️ 4 September 2025
⏱️ 84 minutes
🧾️ Download transcript
Summary
Welcome back to Stick to Football, brought to you by ARNE.
In this episode, Gary Neville, Jamie Carragher, Roy Keane, Jill Scott and Ian Wright are joined by former Leeds and Chelsea striker Jimmy Floyd Hasselbaink to look back on a career packed with goals, big moments and unforgettable stories, as well as his time as a national team coach and manager in the EFL.
We start with Jimmy’s early career, from growing up playing football to his big break in Portugal. How did he make his way to England and what challenges did he overcome along the journey?
The conversation then turns to his time at Leeds United, how he adapted to Premier League life, the teammates who pushed him to become one of the club’s top scorers, and the controversy around his exit from Elland Road which saw him move to Atlético Madrid.
Jimmy recalls his return to England, leading the line for Chelsea and later Middlesbrough, where he worked with Gareth Southgate. That connection eventually led to him joining Southgate’s coaching staff for Euro 2024.
We dive into the tournament itself. Where did England go wrong, and was playing Trent Alexander-Arnold in midfield too big a gamble? Looking ahead, we also discuss Thomas Tuchel's appointment as England prepare for the future.
Who is your favourite Premier League striker of all time? Let us know in the comments, and don’t forget to like and subscribe so you never miss new content from The Overlap.
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Transcript
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| 0:00.0 | Just before we get started, a quick thanks to our partners and clothing. |
| 0:04.1 | We hope you enjoy the show. |
| 0:06.4 | This episode of Stick to Football is brought to you by Shopify. |
| 0:10.7 | When I first made the move from playing to Punditri, it was a bit full on. |
| 0:15.0 | Suddenly, I was juggling loads of new things. |
| 0:17.9 | It was exciting, but there was a lot to get my head around. |
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| 1:31.9 | Jimmy, come on. Come on join us. |
| 1:34.7 | Danny's got somewhere to be. |
| 1:36.8 | Yes, me too. |
| 1:38.5 | Where'd you have to be, Jimmy? |
... |
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