Well-known member
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 .

Any one also any thoughts on what if moments?

Be a miracle if 1981 and Norman Bell doest rear his ugly head on here.
1,Relegation with emo and the like .... think Robbo lost the plot
2,karankas lost season in the premiership.... what was that all about
3, numerous FA cup games where we got stage fright -- yes Wolves , Orient in particular
4. Selling hugh mcIlmoyle ... gutted at the time although seems to have been hughies issues that was the cause
5 Jackie failing to sign a striker ..... paul mariner or mcDonald
Last edited:
The season in the PL under Karanka and the following season in the Championship.

If we'd sold Ramirez and signed one of Karanka's targets I think there's a chance Karanka wouldn't have lost the plot, and we may have stayed up.

It also still frustrates me that we got it so wrong the following season in the Championship. We already had a squad capable of taking us up, just needed one or two quality additions but spending £50m to more or less build a new team was crackers. It was literally a case of spending the money because we had it and felt we had to spend it.
Yes, the 3 points really hurt our development, but we did bounce back the following season.
Not getting the penalty for a blatant push on Viduka when we were 1-0 down to Sevilla at Eindhoven could have stopped us winning that trophy - and missing out on a Super Cup tie against Barcelona in the South of France.
We had a great team in 1914 and 1939 which never got the chance to flourish.
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.
Sigh - what a depressing thread!
3 points definitely

Cardiff FA Cup 2008

The era 2006-2013.....just a big, huge slump. Until Karanka it was just doing enough to get by and surviving (no slur on Mogga btw)

So soon after 2004 and Europe was just......😫😫
Birmingham, Liverpool, Orient, Cardiff in the FA cup Qtrs were bad, as was man city in the league cup semi.
But for sheer gut wrenching, ecstacy to agony, the 97 league cup final at old Wembley was the worst.
In recent times I’d say the way we went about karankas premier league season. Absolute damp squib.

The playoff final against norwich before that. 2-0 down after sleepwalking onto the pitch.

The Cardiff game. Wow! Disappointing.

The 3 points debacle. You just can’t get your head around that situation happening.

The team robbo got relegated, juninho crying on the pitch at Leeds and being helped to his feet by big bri. That and not holding on against leicester. If they had not happened I genuinely believe that we would now be a consistent top half prem team, maybe even battling for Europe regularly.

My big personal regret was not going to any of the Europe away games. I was living away with the army at the time and watched the final in basra!! I did manage to get a few cans of strong bow and convert our local labour guy , Abbas, to being a Boro fan despite him having his Real Madrid shirt on 😂
Surely got to be the 1997 League Cup final, avoid that last minute equaliser.

We only won 1 game of the last 7 league matches after that and obviously went down, a win in that final could maybe have inspired us towards picking up the 1 additional win that would have kept us up.

If not, we'd have our first trophy 7 years earlier and it would improve our reputation even with relegation.
3 points.... To think we just didn't turn up for the match. You simply can't understand it. I watched an interview with Robbie Mustoe and he said all the players wanted to play it.

Cardiff... Just a missed opportunity.

The playoff final against Norwich. A classic case of 'didn't turn up'.

Then after getting promoted we had a frankly bizarre season in the prem. It's absolutely forgettable. Just a complete waste of time. We went down with a whimper. Absolutely no kitchen sink mentality.
You could say had we stopped up in 88/89 our history could have shaped up to be alot different

Had pears not got injured or we'd signed someone other than Peter Davenport we could have been north east topdogs for a few years until Newcastle's revival

The firesale of Downing, Alves, Huth, Tuncay and later Adam Johnson would we have bounced straight back

Replacing Southgate with Strachan that set the club back many years

Leaving Ayresome Park but like Sunderland the time was right
Selling Brian Clough to Sunderland.
I seem to remember that Boro then sold Alan Peacock ( who had given up his number 10 shirt and donned the number 9 ) to Leeds.
Boro then seemed to plod on for a decade or so finishing 4th a couple of times in the old Second Division until we reached better times.
I agree the Leicester game, had we won then there wouldn't have been a replay and we wouldn't have rested Juninho against Sunderland. I think missing out on the cup hit us hard. I personally think the 3 points galvanised us, we went on a pretty decent run, that Sunderland game was a massive 6 pointer.