BIGGEST EVER BORO REGRET

There's been a fair few in my lifetime. I wasn't old enough for the cup finals. Got into football like 2000.

The PL season Karanka - Catalogue of errors from January onwards. To bring in Gestede and Guedioura was just hideous business. He was so desperate for a Winger but we didn't give him one, we focused on Snodgrass, Bojan and Deolofeou (however you spell it) and got none but didn't turn our attention to any others. Our defence was solid and midfield was okay but we has barely any service to Negredo. I think If we'd have got 1 maybe 2 wingers we'd have stayed up and progressed from there.
We should have sold Ramirez for a huge profit to.

Appointing Agnew. We basically just gave up even though staying up was very feasible. We should've gone and appointed a proven firefighter and got us out of the short term mess and went again in the summer. We had a very capable squad.

Giving Monk the transfer war chest. Monk never seemed the right appointment. To give him the money we did on the signings he did was criminal. I'll forever be happy we got Howson but the rest barring Randolph were absolutely useless.

Letting Pulis sell Bamford but keep Gestede, absolutely hideous. Should've put our foot down and told him to do one.

Appointing Woodgage after Pulis. I love Woody, and I really hope one day he proves us all wrong but to give him the job and only give him 3 very inexperienced championship signings was a dreadful decision. He's an excellent coach though and I'm haply he's back.

Cardiff 2008. All the big teams were out and we basically had the biggest chance ever to win it. We failed.

Mcclaren announcing his England appointment before the final. I think it threw the players off and we got battered.

Appointing Southgate after Mcclaren. Similar to Woodgate. But dumbing down your investment and expecting a rookie manager to turn water into wine was just terrible judgment

Gordon Strachans Scottish escapade. Nuff said
 
The Summer Transfer Window of 2008

the Summer of 2008 was the worst transfer window we have ever had in my opinion.. made worse with a dreadful January 2009 window.

Out went Boateng, Cattermole & Young for £10m and we brought in Emnes, Digard & Hoyte at £10.2m to replace them. Gretar Steinsson was the man who was to replace Luke Young but we dithered and got caught out

Schwarzer leaving on a free and us being unable to bring in Charles Itandje (from Liverpool) left us with Ross Turnbull spent 4 seasons at Chelsea after leaving boro Brad Jones spent 5 seasons at Liverpool, they had nothing to do with the number of goals we scored that season.

We turned our noses up at Nemanja Matic for nearly £1m and stuck with Ben Watson as our only midfield transfer option.

Injuries to David Wheater and Didier Digard cost us more than our choice of keeper. To be honest Lee Cattermole's kick on Didier Digard could be the one single moment that relegated us. The fact that we were unable to bring in a decent midfielder in January was the biggest concern. We were VERY VERY poor in the transfer market.

All this is made 10 times worse when we know that we turned our noses up at Charlie Adam(£500k), Graham Dorrans (£100k), Steven Fletcher (£1m) & Ross McCormack (£120k)

We were poor in the transfer market, we paid over the odds for tripe and refused to pay buttons for talent. We did not have sufficient cover for all positions.

The next season we appointed Gordon Strachan..
 
The 74/75 season for me, we should of won the league that year, even Shankly thought we would.
In the end Derby won it beating us by 5 points.
We drew with Derby 1:1 at Ayresome.
I had a signed ball from both the teams it annoyed me so much I gave it to my nephew.
 
Ref the 1996/7 season

Even after the Blackburn 3 points deduction - the club chose to sell Fjoftoft leaving them reliant on only 2 strikers Rav and Beck and with masses of cup games to come. That was a big mistake in my eyes.
 
Three points.
We were treated so unfairly by the very people in charge of fair play.
The message is clear
Football authorities are bent.
Some clubs they like and others they dont.
We make an unintentional mistake and get docked points to relegate us
A few years later west ham deliberately break rules and get a little pat on the head.
Bury needed 12 million. That's one jed Spence. Deadline day came and they are out.
Derby owed 60 million. Deadlines came and went But they were allowed to continue.
I try not to let it get to me but it still makes me mad.
I am a bitter and twisted man.
 
Canyoudigit said:
After 46 years of going to watch the Boro,there have been a monumental number of if only moments, the obvious one that springs to mind is the failure to turn up at Blackburn and the ensuing 3 point deduction.

My biggest one however will always be the league Cup final at Wembley against Leicester and our failure to see the game out which in my opinion would have opened the floodgates to a period of sustained top flight success .

I agree with this (and the 3 points debacle). But I also think re Leicester at Wembley, that even to lose the match within normal time would have had a much better outcome.
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The UEFA final for me. Another trophy in the bag, Guaranteed entry into the next year's competition and a mouthwatering Super Cup final against Barca would have beckoned...
 
My personal biggest regret was giving Man City FA cup tickets (0-2) at the Etihad away to the spark who was working on my house at the time as I was on a tight schedule. Bittersweet listening on radio when I should have been in that away end scarring my shins.
 
SmogonOuseburn said:
Finally, interviewing Bill Shankley in 1950s then offering him the job, and then back-tracking on it could have been the biggest regret. Liverpool were in 2nd Division as well and he set them on a path of glory.
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I think there was a bit more to it than that.
I remember reading Shankly's own account of it (did someone post it on here?).
He was all set to join Boro but his current chairman had aspirations within the FA and for some reason was told not to let him join us .....or else.
Something like that anyway.
 
Personally, my biggest regret is my boss refusing to give me a day off (even unpaid) for the UEFA cup final as he "didn't want to create a precedent". My wife, mum, dad and brother-in-law all went and I gave my ticket to The Goat off the original FMTTM.
 
I'd say more the failure to strengthen appropriately in the summer that ultimately led to the relegation in 96/97. Spending 7 mil on Rav was great but with Juninho supplying the bullets any half decent striker would have got a decent amount of goals.

Starting the season with Miller/Walsh/Roberts as our keepers and Vickers/Whtye/Pearson/Whelan as our centre halves was criminal!!!
 
Redwurzel said:
Ref the 1996/7 season

Even after the Blackburn 3 points deduction - the club chose to sell Fjoftoft leaving them reliant on only 2 strikers Rav and Beck and with masses of cup games to come. That was a big mistake in my eyes.
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It still bothers me now that Beck got in the team that season ahead of Fjortoft. Big Jan was much better and would have been a real foil for Rav (when we played 2 up front)
 
MickaelDebevePhenomenal said:
I'd say more the failure to strengthen appropriately in the summer that ultimately led to the relegation in 96/97. Spending 7 mil on Rav was great but with Juninho supplying the bullets any half decent striker would have got a decent amount of goals.

Starting the season with Miller/Walsh/Roberts as our keepers and Vickers/Whtye/Pearson/Whelan as our centre halves was criminal!!!
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I remember Vickers and Whyte looked awful without Pearson. Pearson getting injured early in the season made our defence awful until he returned and we bought Festa and Schwarzer.
 
As mentioned above, the preparation for 2008 was dire.

I also often wonder if the team bus not getting stuck and arriving to Wembley on time against Norwich might have changed the outcome of the playoff final
 
I always go back to March 1975 St Andrews FA Cup Quarter Final.

We were on top form, had beaten Birmingham comfortable twice already and Fulham were awaiting in the semi final who were 2nd division. Jack played an ultra cautious game and it backfired. That was my what if moment.
 
Selling Souness (albeit for a lot of money-£330,000??) really upset me as a young supporter. I don’t think I have ever seen a better all round player at the Boro.
 
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