Most gutted you have ever been as a Boro fan

[Redlips]

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.

 

[Jedi boro]

I agree as Yes not even in my top 5 last night.

 

[Madeinbrazil]

Only disagreement I have is that the Seville game we should have had a penalty at 1-0

 

[homesickblues]

Last night will take some beating, and I go back to Wolves in the FA Cup.
I was sensing that we had the makings of a good squad, and this was a great chance that will be hard to replicate.

 

[Madeinbrazil]

Loosing 2 cup finals & getting relegated 97 Has to come top.

 

[Legz]

Definitely Cardiff

 

[Diego]

Relegation at any time tops all of them for me. Can take getting beat in big games as you get over it eventually but the sadness of relegation lasts a long time.

 

[RandyGrandad]

Every time I fancy a decent pint at the bar in the ground.

Rubbishbeeruntastic

 

[Uwefuchs]

Heskey and nothing else comes remotely close

 

[joeydiaz]

Emile Heskey’s equaliser. I hope I never experience that pain again.

 

[Alzi]

Cardiff given that was probably the best chance in our history to potentially win the FA Cup. Awful performance.

The late Peter Whittingham was superb for them.

 

[the_holgate_roof]

League Cup final against Leicester, Heskey equaliser.

 

[El Guapo]

Wolves ‘81 and the end of 96/97 2 finals and relegation.

 

[masquesmog]

League Cup final against Leicester, Heskey equaliser.

and didn't Mark Robins take the corner?

 

[parmoboy]

Last night ranks highly as one of my biggest disappointments as a Boro fan.

After drawing at their place the tie was set up perfectly for us. It was disappointing enough to lose but we went out with a whimper, which makes it even worse.

I didn't go to the Norwich game so I was desperate to see my team at Wembley for the first time. Hope I get another opportunity.

 

[Mickey_2003]

Euro cup final, definitely.
Then the Leicester.
Then the Cardiff game.

 

[northriding]

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.

 

[indeedido]

Christ some shockers to choose from.
Wolves in 81 FAC 6RR
Cardiff QF
Heskey equaliser and Claridge winner at Hillsborough in LCF
Di Matteo atmosphere hoover at Wembley.
Sevilla last ten minutes.
Harewood for West Ham in 06 FA SF.
Giggs winner in League Cup SF 2nd leg and Schmeicel save from Falconer
Norwich play off no show.
Villa Park pulis handbrake.
Relegation at Elland Rd.
Relegation from top flight at Hillsborough
Last night's whimper (well put parmoboy).

But my biggest was relegation to third tier at Shrewsbury and the knowledge we were going out of existence. No feeling like being told you have a terminal illness.
And then no relief like being told you are going to live after all.

 

[Kowalski]

When they put the locks on Ayresome Park.

 

[Nano]

Looking back on last night is even worse than it was yesterday. If we could have picked our playoff contenders with us then Coventry, Luton and Sunderland would have been top choices. Don't think you could pick an easier set of fixtures from the realistic contenders. We were easily the best team of the 4 so to not even get to the final is very disappointing.

That Leeds game in 97 is comfortably the worst though. It was such a big "what if" moment if we could've just avoided relegation. We played some ridiculously good football, there's no way we should have been relegated. It was devastating.