Losing at home to York City in April 76, they had only won one away game all season and had a bigger freak than Peter Crouch called Jimmy Hinch, he scored a goal against us that night

That semi final home loss to Everton.

Nothing can compare to Aldershot 87 for me

Trannys in the play off final.

 

The Barry Knight Match. Long trip home was that.

 

Southampton Replay in the Cup. An even longer trip.

 

Villa FA Cup Semi. If it wasn't for Holdsworths miss i might have coped better.

 

Stoke FA Cup Semi. Embarrassing as well as gutting.

 

Coventry at home in a Premier league 6 pointer 0-4.

 

Wolves beating us at home when Kenny Hibbitt scored.

 

You have to put up with the rain to enjoy the rainbows.

Not as gutting as all of above but I was pretty upset when Sporting Lisbon beat us. The combination of knowing what might have been and accepting we are not likely to see Europe again pissed me right off,

The superbok with Port chasers afterwards didn’t half finish me off

Good question this.  Apart from the obvious hammerings and one off big games, there are those matches when you'll be on your way home and just think "FFS Bolton!" & be annoyed for the rest of the weekend.

Rotherham (a) 91.  Conceding a last minute equaliser that totally derailed our promotion chase.

Oldham (h) 94 FA Cup.  When you think of the sides we'd beaten to get to the Quarter finals, we'd landed the kindest draw against a then struggling Premier league side.  I don't recall them offering anything that day, we'd passed them off the park but just couldn't break them down.  One simple mistake from Paddy and we were out.

Marseille (a) UEFA cup. I'd really begun to believe that our name was on the cup that year.  

Too many to remember. The last one I felt completely fucked off at was Burton away the week before Forest. 

Agree with most above 

but for me Middlesbrough at Cardiff got to me 

So close to seeing us win a major trophy and we didn’t turn up 

 

Sunderland home 98. Think we were unbeaten at the time. Had all of the ball and lost three nil. English teacher was a Sunderland supporter and gave us hell about it. 

Their are so many to choose from over some 50 odd years but one that sticks out for me was Oldham in that 6th round FA cup , after seeing off so many big guns and then being set up for a go at united at Wembley was gutting. 

This could be another 1000 page thread 😊

Anniversary of 2 of them today according to BN, Liverpool in coca cola cup final and Villa in the fa cup semi.

So many games have left me dejected in last 10 or so years that they shouldn't really hurt anymore, Blackpool at home 2-2, 7-1s at Reading/Accrington, 5-2 at Wigan really took a few days to get over, Burton just before the Forest miracle. There'll be loads more from this post PL era I've forgotten about.

Lisbon was insulting, I'd probably feel even worse if I'd have gone, twattings off United down the years, relegation games etc.

Still think it's the Stoke semi final for me though, that might be the only one I've come away from and spent days and days genuinely thinking "do I really want to do this anymore?".

Gonna flip this a little. 

 

Leicester 5-0

 

I got as far as Sheffield with ticket in hand

Stoke was devastating, Lisbon was a good trip spoiled by team selection made far more insulting when we lay down to 10 man Wigan on the Sunday. 

All of the times when it really matters and we fail ,but an insignificant "Gutted" game was when we failed to relegate Birmingham on last game of the season after leading 2-0.

We were weak as pi$$ prior to that game and all of the season after, and ever since TBH.

For me it's got to be the Stoke FA Cup semi final at Wembley.

That defeat was the start of our rapid demise, from which we have never recovered.

 

Losing 2-1 at home to QPR in 18/19 really affected me for some reason. I was fucking devastated.

Besides the obvious ones, I was really upset by the 4-2 home defeat by Arsenal.

Leading  by 2 and then just seeing them scoring 1 by 1.

I was slumped back nearly crying  - at my age, I shudda known better. 😢

Wolves, New Year's Eve. Think we drew 1-1, Sam Ricketts scored a belter. I knew then we were down, and it fucked up my celebrations

Black Sunday & the spineless relegation at Chelsea probably upset me the most. Of the Stoke games, the relegation hurt more than the embarassment at Wembley.......for me, relegations when we've had the chance to escape, are worse than the short term sickener of a cup defeat.

Chelsea away 98 to relegate us , I really thought we might get something that day , we huffed and puffed . I remember at 1-0 near the end , Frandsen went on a solo run and the Chelsea fans were even willing him on to score.

Oldham in the cup , all them great performances and we lose to them shithouses at home.

Ipswich away in the play - offs , so many emotions that night and then to get totally cheated , following by them wankers on the pitch taunting us 

Edited April 2, 20206 yr by dusan nikolic

6 minutes ago, bolton va va said:

Black Sunday & the spineless relegation at Chelsea probably upset me the most. Of the Stoke games, the relegation hurt more than the embarassment at Wembley.......for me, relegations when we've had the chance to escape, are worse than the short term sickener of a cup defeat.

Chelsea the only time I’d say a mans head disappeared into his body. Gilanzza grrrrr

agree with Chelsea and Oldham, we were 1 win away from it being so much better

another one I always remember being devastated about was Derby at home in 2001/02 season - it was a 6 pointer in March and when they did us 3-1 I thought that was it, we were going down, again, and we'd never be a PL team

then Djorkeaff arrived officially a week later and everything was ok

missing athletio madrid, was on a family holiday in florida

only euro i missed

8 minutes ago, ZicoKelly said:

agree with Chelsea and Oldham, we were 1 win away from it being so much better

another one I always remember being devastated about was Derby at home in 2001/02 season - it was a 6 pointer in March and when they did us 3-1 I thought that was it, we were going down, again, and we'd never be a PL team

then Djorkeaff arrived officially a week later and everything was ok

Yep , I remember being in the concourse at the end sat down with my head in my hands for 20 minutes , half pissed and on the verge of tears.

Didn't that grey haired tosser ravanelli score one.

Edited April 2, 20206 yr by dusan nikolic

Losing to Chelsea wasn't spineless we did what we could that day -  we should have stayed up comfortably that season but we lacked proper organisation and threw too many points away. Even then we were cheated out of it. 

Oldham for me sticks out. Would have been a semi against Man Utd - we'd battered them for first 20 minutes or so - could have easily been 2-0 up but they hung in there without doing much - they were exactly the sort of rubbish side we struggled against in that period - we did better against stronger sides. It was just a gutting way to lose.

However, I don't think I've been more gutted than losing to Villa in the semi. Chance of an FA Cup final and we really, really should have won.