I'd say in my time supporting the Chelsea, the most disappointing year following our great club was probably 1999. Being a younger fan, I haven't experienced relegations and just about avoiding the drop into the 3rd tier etc but I honestly can't think of a more depressing year than 1999.

The 1998/99 season was one of real highs/lows. It was almost typical Chelsea in that they build you up to let you down again. Against all odds, we emerged as title contenders and I genuinely believed we could break up this duopoly of United and Arsenal that was fast emerging. The 2-2 with Leicester still haunts me to this day and I still believe we'd have won the league if we'd held on. I don't know what Vialli was thinking and then of course losing at home to West Ham before that hindered our chances even more.

After that near miss, I was more excited than ever for the 1999/00 season as I honestly believed United and Arsenal would decline and we would get even better and not make mistakes like we had in the previous season, but it was never to be. That was the season we lost three games on the trot, and our hopes we all but dashed by Christmas.

Some games in the first part of that season live in my memory and I remember feeling utterly despressed:

Derby 3-1 Chelsea - Totally outplayed

Chelsea 2-3 Arsenal - "That game"

Sunderland 4-1 Chelsea - "That Kevin Phillips goal"

And then to top it all off, that stupid 2-0 home loss to Dirty Leeds which was 2 days before my Birthday

Thankfully we went on to win the FA Cup that season but the 5-0 win over Manure was just a cat amongst the pigeons. That season turned me into the pessimist I am today with all things Chelsea related.

Anyone else like to share their stories on what their worst season was as a Chelsea fan?

Well my first season of actually fully paying attention and listening to every game was the 02/03 season (started at the end of the 01/02 season), and everything since then has been pretty good really considering. But this season has been very disappointing, if only because we were very good last year and we expected more of the same this year but with younger players being sowly integrated into the squad, and all we got was months and months of crap, then the youth loaned out. But hopefully it can end well to make up for it.

Not sure if much beats the way we started this term,every pundit said we were shoe-ins so early,scoring huge totals,then a blip that turned to an avalanche of disappointment,and all with the same players,now it looks like we will finish like we started empty handed but on fire.oh for the fickleness of the premier league.

Relegation play off vs Boro, when I was a kid.

Recently, Ranieri losing the plot vs Monaco, Champs League final under Grant, & the way this season has imploded.

1974/75. I watched us win one game (in the FA cup) all season. I missed the ones where we did win and watched a lot that we didn't.

1978/79 I think. Whichever one it was when we got relegated again. I know I got pissed a lot just to forget.

The 80's were also terrible. Again a lot of my time off my face. The term "drowning your sorrows" rang so true, for me. Basically I spent the vast majority of the 80's depressed and pissed etc.

When people say we have had a bad season I have to remember that in recent history I suppose it might be but I take nothing for granted and any win is a good win.

Difficult question, there's been so many disappointing seasons for us Chelsea fans. After much deliberation, I'm gonna go with the 1974/75 season.

The manager, Dave Sexton, had already sold our two greatest players because he was sh*te at man-management and couldn't control them - Alan Hudson went to Stoke in January 1974, while Peter Osgood went to Southampton two months later.

1974/75 began with a 0-2 defeat at home to Carlisle, which kind of set the tone for the season ahead. Some notable results that followed were, in the league: -

lost at...Derby 1-4...Newcastle 0-5...Wolves 1-7...Stoke 0-3...Tottenham 0-2...and home to QPR 0-3.

We also got stuffed 2-6 at Stoke in the League Cup 3rd round replay

We got relegated in 21st place, winning just 9 games out of 42. Our top scorer in the league was Ian Hutchinson - with 7 goals.

A truly appalling season, for which I almost entirely blame Dave Sexton, who was eventually sacked in October 1974. The board have to take some blame too, as they should have sacked him about a year or two before. Sexton was temporarily replaced by his assistant Ron Suart until April 1975, when Eddie McCreadie was brought in to oversee the last few games of the season.

Another terrible thing about this season was that I went to almost every game, home and away - no man should have to suffer like that!

I started following the club in 1982, when I was 6,(thanks to my dad), so this season was definately not my worst. In fact I am still grateful of the fact that we have such a strong side that I know will be major contenders in every competition next season.

87/88 was about as dissmal as it's ever been.

We became the first top division club in 90 years to be relegated from the top tier by way of playoffs when we lost to 2nd division M'boro.

The same season:

English clubs in their third year of the European ban.

Liverpool manager Kenny Dalglish added the league title to his managerial CV to bring his total of championships to two in three seasons and Liverpool's all-time total to 17.

Alex Ferguson's efforts in rebuilding Manchester United saw them finished second in the league just 18 months after they had looked in danger of relegation.

Liverpool striker John Aldridge was top scorer in the league and collected a championship medal in his first full season at the club.

Newcastle United's exciting young midfielder Paul Gascoigne was voted Young Player of the Year before being transferred to Tottenham Hotspur.

England were eliminated from Euro 88 after losing all three group games in West Germany.

Liverpool paid an English club record fee of £1.9million for Newcastle United's 26-year-old striker Peter Beardsley. They also spent £900,000 on Watford winger John Barnes.

The seasons where Geoff Hurst and Danny Blanchflower were in charge. What a pair of c**ts, especially the latter. Bluebeard's season also spings to mind but I wasn't a regular goer then although I went to quite a few, that came when these pair of w**kers were in charge.

Edited April 27, 201114 yr by Peckham Blue

87-88 for me too.

Too young to recall previous relegations. Oxford away in 88 was as dismal and as depressed I've ever been after a game. The day we knew we were in big trouble.

1974/75. I watched us win one game (in the FA cup) all season. I missed the ones where we did win and watched a lot that we didn't.

1978/79 I think. Whichever one it was when we got relegated again. I know I got pissed a lot just to forget.

The 80's were also terrible. Again a lot of my time off my face. The term "drowning your sorrows" rang so true, for me. Basically I spent the vast majority of the 80's depressed and pissed etc.

When people say we have had a bad season I have to remember that in recent history I suppose it might be but I take nothing for granted and any win is a good win.

1978/79 for me, I had just left school and shelled out £25 for a standing season ticket with my first months pay. Finished rock bottom with the only highlights being the famous 4-3 win at home to Bolton and if memory serves me correctly conceding 5 at Highbury but watching the boys take the Northbank :)

I also went to Forest away (0-6) and Ipswich (1-5). I swore I would never go again after that Forest game (as I did after the recent Man Utd champions league game and many more in between!)

74-75 season for me too.... I was 14 and had been going down to the bridge for a couple of years and had become a 'shed-end' regular, and like shedhead i never saw us win a single game all season, the most depressing being in the shed watching us get thumped 3-0 by the dippers, only consolation was (as i recall) a mob of Chelsea caused a right rumpus in the North stand !

All in all a real sh*te season...

That's why i'll always be thankfull for what RA has done for us, that 74-75 season (and similar seasons) just seem a million miles away from us now.

Alan

Last night reminded me how gutted I was we got done by Uefalona in the champs league.

As with many others 87/88 is the one that I remember giving me the most emotional pain. I was 13/14 and can still remember just how upset I was even now.

Edited April 28, 201114 yr by dkw

78/79. Though being there for the comeback 4-3 win over Bolton is a memory that will always stay with me.

And in a different era with massively different expectations, this season is a very disappointing one too. Especially given the resources at our disposal and the flyer we had at the beginning, to come away empty handed on all fronts can only be viewed as a failure.

78-79 was horrendous. Having come up from Div 2 ahead of Notts Forest just 2 years before, we had to watch them win the League and follow it up with the European Cup. We had a great young side but lost our manager over a club car he wanted. Shellito was out of his depth and things just went downhill.

Apart from us being crap (and I was there in the 0-6 v Forest, too, Teabar), the really scary thing was that we were completely skint, you knew we'd lose our best players when we went down (we did), and we had a total idiot in charge (Blanchflower). The future looked even worse than the present back then - and so it proved as we nearly went down to Div 3 a few years later.

Blimey ! You young'uns are lucky not to have been around in the dismal seventies. After the highs of the first FA cup win in '70 and the following European success there only seemed to be one way - down ! Given as well the general blight of that decade and the economic downturns of the country, it was pretty grim.

Nowadays it's a sheer pleasure to see Chelsea where they are. You gotta suffer years in the wilderness to appreciate being a top club now.

Long may we reign.........

93-94. Wembley. Man Utd.

Two seasons for me:

74/75 - had a season ticket in the brand new East Stand, spanking view but the only problem was it was a view to watch absolute crap. Should have seen the signs in the very first game against Carlisle where we lost 2-0.

75-76 - the season where I started working and having chosen to go into retail this meant I very rarely got to see Chelsea play (for the next few years as well in fact - only managed 2-3 games a season)

Only supported since 95 and then I was abit too young to let it really effect me but personally the worst season for me was when we lost the league cup final to the Spuds and the Champions League final to Man U. Its was just such a heartbreaking season and I still can't watch anything of that night in Moscow.

As for heartbreaking games:

Champions League semis against Liverpool (both that we lost) and that semi against Barca where we were robbed

Getting hammered by Spurs in the league cup semis in 03 (right?) although we did get sweet revenge much later

Losing to Arsenal at the Emirates in 07 when that cnut Gallas scored

Losing to Man U in Europe this year was heartbreaking aswell

Chelsea 2 Arsenal 3, we should have won this game still don't know how we didn't

Chelsea 0 Liverpool 1 - goodbye home unbeaten run I would have rather lost it to almost anyone than them

I'm sure there's alot more but I can't think of anymore right now

Edited April 30, 201114 yr by Bobbywoodhogan

As I started supporting in late 90s then for me it was 2000/01. After the FA cup win and good run in our first season in the CL I had high hopes for the next season. We won the community shield but that was about it. Vialli got sacked pretty fast and in came Ranieri who couldn´t really get it going in his first year.

Been following since 96/97. Of the top of my head the semi final against moncaco. We should have won it that year. Would mourhino have came though if we did?

To be honest alot the heartbreaks we have had have usually led to us winning something later or effecting the club in a positive way afterwards.