Arsenal Rewind 1998-99: Heartbreak Hotel as Leeds celebrate beating Arsenal as Manchester United win Premier League title by single point 

Ahead of Arsenal vs Leeds here's the brilliant Steve Pye - aka That 1980s Sports Blog - as he recalls the crushing end to the 1998-99 season, including Gunners damaging defeat at Elland Road to hand Manchester United Premier League title 

Being so invested in the fortunes of a club can be exhausting.

Be honest, how many hours of your life do you find yourself thinking about The Arsenal, our fixtures, injuries, suspensions, refereeing appointments, VAR controversies, and so many other things that you have no control over. The internet and social media hardly help.

A title run-in can be the most draining of experiences.

Sometimes you just know everything is going to be alright. In 1991, 2002 and 2004, I had every confidence that we would get over the line.

In 1989 and 1998, less so, the former down to squad inexperience and the latter due to the recent title winning credentials of our Manchester rivals.

The feeling of euphoria when you get the job done is joyous.

But what about the ones that got away?

Sadly, the pain of unsuccessful title campaigns never seems to ease.

I still shudder at the thought of Bolton in 2003, and how I left the ground that day knowing deep down that we had blown it.

Although it hurt at the time, I always feel some good came out of that collapse in 2002-03. Just like the Michael Owen mugging of 2001 in Cardiff, the desolation felt by the players proved the motivation for what followed.

I have no doubt that Cardiff led to winning the double at Old Trafford and the Invincibles were possibly born when somehow Manchester United won the league in 2003.

But there is still one league title that I cannot get over.

Losing the Premier League to Manchester United by a solitary point in 1998-99 hurt then, hurt in the immediate aftermath, and still hurts now.

The fact that they went on to win the treble added to the misery.

Let’s get it right: it is surely better to be in the race than not at all.

We went close in 2008 and flirted a little in 2010 and 2011, but mostly the battle for top four has been our main aim post-2004. 

The problem is that you don’t always get what you want.

In the 1998-99 season, Arsenal played some sublime football, possibly exceeding the displays in the previous double winning campaign.

After a damaging 3-2 defeat at Villa Park in December 1998, the team embarked on a 19-match unbeaten run in the league and surged to the FA Cup semi-finals.

The issue was that an imposing obstacle was in our path.

Manchester United pretty much matched us blow for blow in the league, and the mother of all showdowns awaited in the FA Cup.

I was privileged enough to be at that replay at Villa Park. Two great rivals, like Frazier and Ali, going at each other. It was one of the greatest games I’ve been too - it is also one of the worst.

The biggest what-if moment relates to Dennis Bergkamp missing that final minute penalty.

Score it and there would have been no double or treble for United. Of course we will never know for sure but had that penalty had gone in then we may have claimed back-to-back doubles. Such are the fine margins in sport.

As I left the ground that night – and I am big enough to admit that I was quite close to tears – I thought that was it for our season.

Thankfully, our players were made of stronger stuff.

Thumping wins over Wimbledon and Middlesbrough, a narrow victory over Derby, and a delicious 3-1 win at White Hart Lane saw us move back to the top of the table.

When news filtered through to the away end at Tottenham back in May 1999, that United had dropped points at Anfield, I thought we were going to win the league. Now you were going to believe us.

All that stood between us and a successful title defence was a tricky looking fixture at Leeds and a Highbury date with Aston Villa.

Leeds 1-0 Arsenal. Elland Road, Tuesday, May 11, 1999. 

I’ve paused for a bit, trying to think of how to describe that trip to Elland Road.

Ian Harte missing a penalty for Leeds. Arsenal creating chance after chance.

Kaba Diawara - ah Kaba Diawara, the name still brings a shudder - unable to find the net when it looked easier to score. Nigel Winterburn injured and being replaced by Nelson Vivas.

Jimmy Floyd-Hasselbaink heading a late winner at the back post.

I’ll never forget the sound of the ball hitting the net in front of me.

Closing my eyes, I knew this time that we were down for.

Leeds’ fans celebrated like they won the Champions League, where in reality they had handed their supposed “rivals” the title.

Upset football fans never let go of baggage - I was delighted when they were relegated in 2004.

Our only hope was to beat Villa and hope Tottenham could prevent United winning at Old Trafford.

When those with radios – yes, this was 1999 – reported that Tottenham had taken the lead, some started singing “Come on you Spurs”. I couldn’t bring myself to do it. As Spurs fans will undoubtedly tell you, you can’t rely on them.

We won 1-0, yet United’s 2-1 win confirmed the first part of their treble.

And that was that.

Nine months of travelling up and down the country – and across Europe – all over, with nothing to show for it.

The main thing that pained me was the fact that I thought we were as good as United, if not better. But to the winner the spoils.

So all I am asking the footballing Gods for is that we don’t go through this again.

Sadly, I don’t think it will be that easy.

But perhaps I should take my own advice and simply appreciate that thanks to Mikel and the boys we will hopefully be in with a sniff of title glory at the end of the 2025-26 season. 

A version of this article appeared in our souvenir 300th printed issue of the Gooner Fanzine. Buy your copy here 

Twitter: @1980sSportsBlog