Most gutted you have ever been as a Boro fan

Most disappointed

Leicester and relegation in 97 at what could have followed

Again disappointed with Norwich it was bad but coventry was far worse at least Norwich played us of the park we lost to much inferior team in Coventry


Most pîssed off
relegation under Southgate

including the Newcastle match where the team had left fighting spirit back at xmas time. I can take losing but just giving up like we did was unforgivable. A team full of yellow belly cowards

The cardiff match again i was very pîssed off more gross managerial incompetence from Southgate.

.
 
Frozen Horse said:
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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Totally agree with your first 2 paragraphs, our Bus may not have got to it's final destination, but what a trip it's been. I haven't seen us play football as good as this season, since Charlton's champions.

The last season in the Premier league was dire, didn't enjoy it much at all.

The most gutted I've been goes back to my youth, when the Boro were or seemed to be the most important thing in my life, it was the 1976 League Cup semi final defeat to Man City. Battered on and off the pitch, Maine Road was a scary place to go in those days.

Anyway, I'm already looking forward to next season, I've got my first cheap over 65 season ticket and I know that walking to our first home game I'll have a big smile on my face just like I did when I went to my first ever game in 1964.

I love the Boro and always will.
 
I remember being really dissapointed we never got Venables as full time manager - twice. After Robson and after McClaren.

Also I am sure after McClaren we also wanted Martin O'Neill, think he even got interviewed. Felt like the right appointment, but it fell through and we got Southgate.
 
the_holgate_roof said:
League Cup final against Leicester, Heskey equaliser.
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Same. I think this was the only time I was gutted. We were so close in a tight game. Even at 11 year old it was a euphoric goal celebration with my Dad.

All the other times - FA Cup Final, Chelsea in the League Cup Final, Eindhoven, Relegations, Norwich - we were never really in it and I just appreciated being in that position in the first place. A lot of English club supporters will never get to have that feeling.
 
It's actually really interesting to see the differing answers. People's answers must depend on so many factors in their life at the time I suppose so there's not just 1 answer fits all.
See I wasn't that disappointed Wednesday night....maybe due to being a boro fan 30+ years now....I've experienced the tears and the vast disappointment in my younger years and am at a time and an age now in my boro supporting life where it still means the world to me but other things are more important, I've experienced crushing defeats etc, maybe it was because even achieving the playoffs was something i never expected in october so having the season we had since then was amazing, or just maybe because I was in agony having had a b***r of a tooth removed lol.
 
Frozen Horse said:
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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I think with the Cardiff game; Chelsea (Barnsley) and Manchester United (Portsmouth) had both been knocked out the day before, surprisingly.

The other Sunday QF was West Brom v Bristol Rovers. So on the Sunday, we were the highest ranked club left in the competition - Portsmouth were down the bottom of the Prem, all the other teams left were either Championship or lower. So if we were favourites to win the cup on Sunday morning, we probably deserved to be.

Then we went out and gave a dogshit performance where the game was effectively over after 25 minutes when the road was wide open. It would have been Barnsley in the semi, Portsmouth in the final. We would have been favourites in both games, just like we were against Cardiff.
 
atomicloonybin aka ALB said:
Portsmouth were down the bottom of the Prem, all the other teams left were either Championship or lower. So if we were favourites to win the cup on Sunday morning, we probably deserved to be.
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They weren't and we didn't. Portsmouth were 3 places and 15 points ahead of us in the PL on the morning of that match. That's a big difference given we only got 42 points all season.

That gap didn't get smaller, and they finish 5 places ahead of us. They actually lost their last 4 league matches that season as they rested players for the cup final, so the gap probably could have been bigger.

They were a better team than us that season and had 1 less round to play on the morning of the Cardiff match. We were not close to being favourites. We still wouldn't have been favourites if we beat Cardiff.

I'm not saying I wasn't gutted by our performance that day, but the myth that the cup was somehow ours for the taking is utter nonsense. The myth has sprung up out of self pity
 
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Man City , Lge Cup semi 1975
Birmingham Fa Cup Qtr final.
Orient Fa Cup Qtr final
Wolves Fa Qtr final
Leicester Lge. Cup final,
Chesterfield Fa Cup Semi final
West Ham Fa Cup Semi final
Sevilla
Cardiff
 
The 1st FA Cup replay 1988 against then champions Everton back when Bruce Rioch was manager. Seconds away from beating them in extra time only to be denied.
 
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Frozen Horse said:
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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My wedding day was also the day of playoff win over Chelsea. Squatting on my haunches listening to my mates transistor radio, when the final whistle went I tried to jump up, but fell over backwards and spilt my pint all over my hired suit. It was worth every penny of having to pay to get it cleaned.
 
gregorgregorovich said:
My wedding day was also the day of playoff win over Chelsea. Squatting on my haunches listening to my mates transistor radio, when the final whistle went I tried to jump up, but fell over backwards and spilt my pint all over my hired suit. It was worth every penny of having to pay to get it cleaned.
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You could have set the record for the world's fastest divorce that day.
 
Frozen Horse said:
They weren't and we didn't. Portsmouth were 3 places and 15 points ahead of us in the PL on the morning of that match. That's a big difference given we only got 42 points all season.

That gap didn't get smaller, and they finish 5 places ahead of us. They actually lost their last 4 league matches that season as they rested players for the cup final, so the gap probably could have been bigger.

They were a better team than us that season and had 1 less round to play on the morning of the Cardiff match. We were not close to being favourites. We still wouldn't have been favourites if we beat Cardiff.

I'm not saying I wasn't gutted by our performance that day, but the myth that the cup was somehow ours for the taking is utter nonsense. The myth has sprung up out of self pity
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Still by far the biggest collective meltdown in the history of this board. The amount of people who kept saying football had 'died' because our players were rubbish, seemingly ignoring the fact that Cardiff too were also playing football with their giant-killing act (of sorts).
 
atypical_boro said:
Still by far the biggest collective meltdown in the history of this board. The amount of people who kept saying football had 'died' because our players were rubbish, seemingly ignoring the fact that Cardiff too were also playing football with their giant-killing act (of sorts).
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Maybe so; I'd still say it was a bit of a wallow in self pity.
 
Leicester League Cup Final for me, win that and we stay up irrespective of the three points. I had even imagined we had won and had pictured my self celebrating, never done that again and the only time as an adult I have been truly gutted.

As a kid the Orient defeat was pretty devastating, but somehow I thought we’ll win the FA Cup eventually, nearly 50 years later am still waiting.
 
Frozen Horse said:
They weren't and we didn't. Portsmouth were 3 places and 15 points ahead of us in the PL on the morning of that match. That's a big difference given we only got 42 points all season.

That gap didn't get smaller, and they finish 5 places ahead of us. They actually lost their last 4 league matches that season as they rested players for the cup final, so the gap probably could have been bigger.

They were a better team than us that season and had 1 less round to play on the morning of the Cardiff match. We were not close to being favourites. We still wouldn't have been favourites if we beat Cardiff.

I'm not saying I wasn't gutted by our performance that day, but the myth that the cup was somehow ours for the taking is utter nonsense. The myth has sprung up out of self pity
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Well done for dispelling one of the biggest myths in Boro history, its often repeated that we'd have won the cup if we'd beaten Cardiff that day which is nonsense. We would have likely gotten to the final but Portsmouth were a better team that season and would have started as favourites.

That Boro team had a very soft centre which the Cardiff game showed, as did relegation the following year.
 
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