Most gutted you have ever been as a Boro fan

Redlips said:
That is what the Coventry game felt like, the Leicester game. I couldn’t see anything other than a win. It never even entered my head that we would lose.
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Yes agree
30 years on and I can handle it a whole lot better

My lad was and still is gutted about Cov
 
1974/75 season………
We had already played Birmingham home and away, we won comfortably in both games 3-0, so drawing them in the cup was great, I was certain Wembley glory beckoned as the cup route looked straightforward, lots of the big boys gone, the cup was ours……… The atmosphere was intimidating, the area a dump, the ground a bigger dump……….. as the game progressed, up jumps Bob Firkin Hatton and a young kid felt the first of what would be many heartbreaking moments following the mighty Boro.

My dear old dad said to a sullen weapy me on the way home “You better get used to this kidda, it is what the Boro do to you” Wise words indeed.

Emile Heskey was indeed a gut wrenching moment of colossal proportions, but by then, that once young boy had suffered so much pain anguish and heartache multiple times over that it had hardened the man in the moment, to such a degree, it was a mere flesh wound.
 
Hearing about what happened to Leo's family in Brazil.
When Juninho left.
The picture of George Friend sat on the bench after his last game.
Getting home late from the match and finding out Southgate had been sacked.
 
I am less gutted about Coventry than I thought I would be; wouldn't make the 5 worst occasions. I'm still competitive and I want us to be promoted, otherwise what's the point?

However:
I don't think I've ever enjoyed being in the 2nd tier as much as I did for long spells this season.
Being in the PL does not mean i enjoy my matches more: I remember that finishing 10th-15th each year in the PL is a depressing sort of existence.
Far from being a grand day out, getting to and from Wembley is an expensive drag. I'd have gone because I want to see the match, but little else about the trip would have appealed.

In answer to the original question, UEFA cup final and relegation at Leeds. On both occasions I thought "we'll never get another chance at this".

Only time I've cried was after Leicester in '88; my first match at AP. The sting was taken out of that by the playoffs afterwards.
 
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Leicester City (Wembley) - Last minute heartache. I can still Heskey running off, celebrating.
Norwich - Wembley. Great weekend, shame about the football.
Leicester at home in 87/88. Won and we would of gone up. (Went up in the Play- offs). Gary McAllister was class that day.
 
Lottowyn said:
The most gutted ? Perhaps a bit historical , but no one could have done anything worse to the fans.
At the time it was like being slapped across the face with a wet fish.
Brian Clough scored a goal a game at Middlesbrough , a guaranteed 40 goals a season , was sold to Sunderland in 1962, thus ensuring Boro was marooned in the old Second Division for another 11 years.
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We never got close to promotion when he was here either, to be fair.

The highest we finished with Clough was 6th, and 6 points off the top at 2 points per win.

Obviously he suspected that our defence was letting on goals on purpose for money, but still.
 
The whole end of that '96/'97 season was horrible with the last-minute Heskey goal, the relegation at Leeds, the FA Cup Final, the 3 points, the loss of Juninho. Had we stayed up, we were in line to sign some amazing players, or so the rumours said.

Already moved on from Wednesday, really. It was bad, but there is hope for next season with Carrick at the helm. Hoping he can learn from this and build his own team to compete.
 
Redlips said:
1. Cardiff in the fa cup. Southgate should have been sacked in the spot
2. Norwich in play off final. Absolute bottle job performance.
3. Sevilla 4-0 mullered in a final

Last night was hard to take but we will go again.
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Leeds - no doubt in my mind being relegated that season stopped the development of the Bryan Robson era. I am sure we would have gone on and become a real force
 
Lottowyn said:
The most gutted ? Perhaps a bit historical , but no one could have done anything worse to the fans.
At the time it was like being slapped across the face with a wet fish.
Brian Clough scored a goal a game at Middlesbrough , a guaranteed 40 goals a season , was sold to Sunderland in 1962, thus ensuring Boro was marooned in the old Second Division for another 11 years.
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My Dad's worst too.
He still hasn't properly got over it.
 
Last night was worse than Cardiff. Whilst that was disappointing it was only a quarter final.
Leeds I kind of expected us to go down.
Sevilla I was happy to be there.

So Coventry ranks quite highly as I expected us to win.

Heskey definitely the worst though.
 
northriding said:
1996/97 season. Not only the cup final defeats and the relegation, but the burning sense of injustice from the likes of the 3 points deduction and Festa's goal in the FA cup final which was 'controversially' ruled out for offside.

From a sporting aspect, that pain and grievance is not something I would ever want to go through again.
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Didn’t Coventry benefit from the 3 points deduction as well. Wouldn’t they have gone down otherwise.
 
Norwich in the final was difficult to take but Wednesday night is right up. Just feels like a huge missed opportunity.

Sevilla was different as I think (most) expected us to get beat?

Getting done by inferior opposition is always more galling.
 
Like a lot on here I have seen a lot happen over the years, and the other night didn't really upset me, there had been too many warning signs in the lead up to it for me to be totally convinced we were going to do it.
The most painful one is Leeds, I blame that entire relegation on Mikkel Becks non attempted poke at goal when the ball was there on the line to be had in the 90th minute which would have made it 2-1.and we could have gone crazy in that away end to shut up the taunts of the Northern Cocks. Instead we stood there got relegated and realised it was gonna be the same at the FA cup final a week later. That week after the relegation is most painful I have ever known it as a Boro fan, the insolvency pre season in 86 was stretched out and didn't have the defining moments as that relegation and ultimately we had the the joy of we are all still in business on the Friday.

I don't think I was the only one to blame Mikkel Beck, driving back to Teesside after the match we saw a coach up ahead of us and it was pulling off from a layby a good 30 miles from Boro and sat by the roadside on a sports bag was Mikkel Beck looking very fed up, Maybe he was getting a lift, maybe he had been getting flak and had decided to get off, I know what I like to think.
 
atomicloonybin aka ALB said:
The usual suspects. I'd add the League Cup defeat against Chelsea in 1998 although we were on our way to promotion. Another, "let's not bother turning up" performance (and Gazza should have been sent off). My friend was inconsolable that day, sobbing that "we'll never win anything, ever". I thought "she's right".
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I think that's very harsh on the cup final team.

We, as a 2nd tier club, took the team who finished 4th in the PL, to extra time. We certainly didn't "not bother turning up"

There's a tendency to overestimate our chances in hindsight: there's a persistent myth that we were favourites to lift the cup in the season we lost to Cardiff. We never were. Likewise, we were distant second favourites vs Chelsea, and it was an achievement to even take it to extra time.
 
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