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‘When we made it 2-1 against Gillingham, I felt something big was happening – I knew I’d get one more chance and told myself I had to keep calm and take it’ – Paul Dickov remembers iconic moment that changed Manchester City history

May 31, 2025
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When it comes to moments that changed the course of Manchester City’s history, there can be few quite as momentous as Paul Dickov’s last-ditch equaliser in the 1999 Division Two play-off final.

City had slid down into the third tier for the very first time two just years on from playing in the Premier League, and came head-to-head with Gillingham in the final with a place in what is now the Championship on the line.

Despite Shaun Goater twice hitting the woodwork for City, the game somehow remained goalless until nine minutes from time, when Carl Asaba gave the Gills a 1-0 lead.


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Paul Dickov details Manchester City’s iconic play-off final

Manchester City put their fans through the wringer at the old Wembley in 1999 (Image credit: Getty Images)

Robert Taylor seemed to have put the game to bed as he doubled Gillingham’s lead in the 87th minute.

City had other ideas, though, and Kevin Horlock set up a tense finale by pulling one back three minutes later.

Classic Highlights! | Gillingham 2-2 Man City | LEGENDS OF ’99 – YouTube
Classic Highlights! | Gillingham 2-2 Man City | LEGENDS OF '99 - YouTube

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Dickov told FourFourTwo: “When Gillingham scored their second, late on, I remember going down on my haunches and looking at the City fans – 40,000 of them – and just praying for a miracle.

“We didn’t know it at the time, but without promotion that season, the club was going to be in really big trouble financially. It was boom or bust.

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“When Kevin Horlock made it 2-1 in the 90th minute, I felt like something big was about to happen.”

And it did: five minutes into stoppage time, City launched the ball forward from their won half, won a knockdown, and worked it to Shaun Goater. He was quickly tackled before he could get his shot off – only for the loose ball to run perfectly into Dickov’s feet inside the box.

Manchester City players celebrate victory over Gillingham in the 1999 Second Division play-off final

Manchester City won the 1999 Division Two play-off final on penalties after sharing a 2-2 draw with Gillingham (Image credit: Getty Images)

Dickov’s quick reactions to peel away from his man and get onto that loose ball was no accident.

The Scot explained: “I thought – no, I knew somehow that I would get one more chance, and I told myself I had to keep calm and take it. The opportunity fell and I didn’t falter.

“When the ball hit the back of the net, I could have burst with all of the emotion in me. Thankfully, we dragged it over the line. Something special happened that day.”

There was no further scoring in extra time, and City went on to win the shootout…despite Dickov missing his own spot kick.

Pep Guardiola at a Manchester City press conference

Pep Guardiola has dropped Paul Dickov’s name on several occasions (Image credit: Getty Images)

Nonetheless, Dickov’s equaliser helped cement his place in City folklore…and a certain manager still brings his name up from time to time.

Pep Guardiola has joked before that if City ever end up relegated to the second tier as a result of the financial charges still hanging over them, he will need to call up Dickov and Mike Summerbee to see them back to the Premier League.

It’s a bit that still hasn’t got old for Dickov, who laughed: “I was sitting in a meeting when that one happened. My phone just started going off – everyone was asking if I had seen him talking about me.

“Pep keeps doing it and it’s always hilarious. I’m almost pinching myself, because he’s arguably the greatest football manager that has ever lived and he’s still mentioning me from time to time.

“I think it shows how dialled into Manchester City and the long history of the football club he actually is.”



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