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Most painful transfers ever 13:01 - Aug 15 with 8057 viewsstickymockwell

Mine was Gaardsoe. I think it finally dawned on me that we were a million miles from the promised land. Dyer and Treacle helped us move forward and went to much larger clubs.
I'm a bit meh about Omari

Give him a ball and a yard of grass
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Most painful transfers ever on 13:02 - Aug 15 with 4709 viewsParisBlue

Taricco 😞

Libraries gave us power
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Most painful transfers ever on 13:03 - Aug 15 with 4694 viewsbluearmy4838

Ian Marshall to Leicester. I'm pretty sure I actually cried when my dad told me.
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Most painful transfers ever on 13:03 - Aug 15 with 4690 viewstractorboy1978

Marcus Stewart hurt.
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Most painful transfers ever on 13:06 - Aug 15 with 4632 viewsFrimleyBlue

Dobra

He never got the 5 mill move to arsenal.



But my most painful was scowcroft.
I absolutely loved him and we really missed him too.

Waka Waka
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Most painful transfers ever on 13:07 - Aug 15 with 4617 viewsMrBeckinsale

Jordan Rhodes.

Dalian Atkinson.

Richard Wright.
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Most painful transfers ever on 13:07 - Aug 15 with 4613 viewsnorfsufblue

Butch to Rangers
Dozzell to Spurs really hurt me tbf
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Most painful transfers ever on 13:09 - Aug 15 with 4581 viewsDarkBrandon

Most painful transfers ever on 13:03 - Aug 15 by bluearmy4838

Ian Marshall to Leicester. I'm pretty sure I actually cried when my dad told me.


I learned about that in the stadium!

I turned to the chap behind me and asked why he wasn't playing.

The kids won't understand, but before the internet and if you lived outside of the area it was easy to miss big ITFC news.
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Most painful transfers ever on 13:09 - Aug 15 with 4575 viewsDarkBrandon

Most painful transfers ever on 13:02 - Aug 15 by ParisBlue

Taricco 😞


Me too.
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Most painful transfers ever on 13:10 - Aug 15 with 4558 viewsBarcaBlue

Terry Butcher to Rangers.

The writing on the wall was there for a couple of years that the glory days were coming to a close. That was just the endpoint.

After Mariner, Muhren, Brazil etc moving on that was the one that signalled a clear before and after for me.
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Most painful transfers ever on 13:11 - Aug 15 with 4550 viewsDarkBrandon

Most painful transfers ever on 13:07 - Aug 15 by norfsufblue

Butch to Rangers
Dozzell to Spurs really hurt me tbf


Oh, yeah. Dozzell to Spurs. Ouch.

It was something of an extended transfer saga over the Sumnmer. Would he sign a contract with us. Would he leave. My gf got so fed up with me banging on about it she phoned the club up to ask what was happening with him!
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Most painful transfers ever on 13:12 - Aug 15 with 4517 viewsGlasgowBlue

The slow drip of departures from the 1981 team.

Sometimes I think about the frothing lunatics I’ve put on ignore, who will have kept replying to me again and again, but I don’t even realise they exist.
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Most painful transfers ever on 13:15 - Aug 15 with 4494 viewsnorfsufblue

Most painful transfers ever on 13:07 - Aug 15 by MrBeckinsale

Jordan Rhodes.

Dalian Atkinson.

Richard Wright.


Jordan Rhodes was just stupidity!
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Most painful transfers ever on 13:17 - Aug 15 with 4484 viewsIllinoisblue

Most painful transfers ever on 13:11 - Aug 15 by DarkBrandon

Oh, yeah. Dozzell to Spurs. Ouch.

It was something of an extended transfer saga over the Sumnmer. Would he sign a contract with us. Would he leave. My gf got so fed up with me banging on about it she phoned the club up to ask what was happening with him!


I hope your GF got answers! The worst thing about the move was Jason claiming to be a lifelong Spurs fans when in a Sun interview the year before he’d claimed to be a Chelsea fan.

62 - 78 - 81
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Most painful transfers ever on 13:20 - Aug 15 with 4442 viewsBrayBlue

Arnold Muhren to Man Utd.

Cheers,
JK
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Most painful transfers ever on 13:23 - Aug 15 with 4400 viewsDarkBrandon

Most painful transfers ever on 13:17 - Aug 15 by Illinoisblue

I hope your GF got answers! The worst thing about the move was Jason claiming to be a lifelong Spurs fans when in a Sun interview the year before he’d claimed to be a Chelsea fan.


Strangely whoever it was on reception she spoke to didn't know (or - less likely - wouldn't say)
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Most painful transfers ever on 13:24 - Aug 15 with 4363 viewsRIPbobby

Gatesy going. He was my hero.
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Most painful transfers ever on 13:26 - Aug 15 with 4353 viewsusm

Mariner to Arsenal

FOYSC
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Most painful transfers ever on 13:28 - Aug 15 with 4329 viewsbelgablue

Alex Mathie to Dundee United

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Most painful transfers ever on 13:29 - Aug 15 with 4320 viewspositivity

mcburnie to ipswich was painful to even contemplate!

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Most painful transfers ever on 13:32 - Aug 15 with 4297 viewsAce_High1

When big Joe made Reuser available on a free, was massively underused post relegation as with his eye for a pass and set piece delivery, the team should have been built around him.
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Most painful transfers ever on 13:40 - Aug 15 with 4222 viewsMarshalls_Mullet

Me too, I remember that one stinging!

A player wanting to leave ITFC for West Brom?! Ouch. The dawn of realisation.

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Most painful transfers ever on 13:41 - Aug 15 with 4200 viewsMarshalls_Mullet

Most painful transfers ever on 13:09 - Aug 15 by DarkBrandon

I learned about that in the stadium!

I turned to the chap behind me and asked why he wasn't playing.

The kids won't understand, but before the internet and if you lived outside of the area it was easy to miss big ITFC news.


Had you not discovered teletext at that point?

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Most painful transfers ever on 13:43 - Aug 15 with 4175 viewsDarkBrandon

Most painful transfers ever on 13:41 - Aug 15 by Marshalls_Mullet

Had you not discovered teletext at that point?


IIRC It was a midweek game, and I'd come straight from work.
[Post edited 15 Aug 2025 13:43]
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Most painful transfers ever on 13:46 - Aug 15 with 4136 viewsNedPlimpton

Neil Alexander weirdly hurt

I wasn't particularly fussed about him but after a few dodgy keepers we looked like we'd found a long term #1 and he leaves after half a season
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Most painful transfers ever on 14:15 - Aug 15 with 4051 viewsitfc_bucks

Most painful transfers ever on 13:46 - Aug 15 by NedPlimpton

Neil Alexander weirdly hurt

I wasn't particularly fussed about him but after a few dodgy keepers we looked like we'd found a long term #1 and he leaves after half a season


Especially for so low a fee.

Matt Holland to Charlton was the one that probably gut punched the hardest.

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