Most gutted you have ever been as a Boro fan

That’s what makes us special as club lads and lasses, the highs and lows go together. Disappointed about Coventry, but I was in Cardiff for my clubs first ever Major Trophy… how many fans can say that.

Imagine being a Man U fan from London only supporting them because they were winning trophies… and now being frustrated with winning very little, I imagine a fair few change allegiance… Urgghh

Who’s the unlucky one… they’ll never get to feel like pure emotional joy we get.

When we win it means something to us because of our lows.

Bring on next season… I can’t wait.

UTB
 
Orient FA cup quarters was my 1st big disappointment, would of played Arsenal in the semis
But there's been a few, as with most club.

To name a few.
Sevilla
Norwich playoff final
Relegation at Leeds Utd 1-1 1997
Chelsea scoring after 42 seconds 1997 FA cup final
 
Leicester at home on the 80’s
Final game of the season to get promoted to Div 1

And we firked it up

Next stop Chelsea in the playoffs - that’s footy in a nutshell
 
I get people saying Sevilla and it was def a push on viduka but let’s be honest they absolutely battered us ( and went on to beat Barca in the super cup in Monaco ) so no disgrace losing that.

The question was most gutted though? Not most embarrassing result.

The chance to win a European trophy (probably the only chance we'll ever get), with one of the strongest Boro sides we've seen.

No disgrace losing to Sevilla as you say, but still a game we had a very real chance of winning. This was a Boro side that was admittedly inconsistent, but had stuffed Chelsea 3-0 and Man United 4-1. They were certainly capable. It was only 4-0 because we had to go kamikaze at the end.

That's why people are saying Sevilla. I was absolutely gutted. After the comebacks it felt like it was meant to be.
 
Leicester at home on the 80’s
Final game of the season to get promoted to Div 1

And we firked it up

Next stop Chelsea in the playoffs - that’s footy in a nutshell
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.
 
In my time supporting it's

Cardiff which was bloody awful.
Relegation in in 09/10, all I'd known was Boro in the prem and it led to such a depressing era
Norwich at Wembley, went to town on the night and it was the quietest I'd ever seen Boro on a Monday night back then.

Honourable mention.
Preston 4-1 Boro. Final day of last season, the feel good factor was there (even with Wilder being seduced by Burnley) and we went to deepdale and got absolutely pummeled and were nowhere near the play offs in the end. That was the catalyst of pure depression until Halloween haha
 
The 2-0 defeat at Charlton in 15/16 is up there for me.

When we beat Derby 2-0 (I think on New Years Day?) that season it felt like automatic promotion was ours to lose. The season ended well of course, but with the Karanka walk-out & lacklustre performance I was sure we had blown it at the time.
 
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.

Mine is Norwich in the play off final. I was too drunk in Eindhoven to remember the game so sadly that doesn’t make my list!
 
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.
 
Easily Leicester for me

Working away from home so wore the area of Teesside on my sleeve and the real chance of a major trophy

Inconsolable afterwards

Also now thinking could add Leeds to that and knowing we`d lose the best player I`ve ever seen wear a Boro shirt, not as bad as Leicester but pretty gutting all the same
 
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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