Gillingham FC have three-fold Wembley inspiration for 2025/26 promotion tilt | OneFootball

Gillingham's three Wembley play-off finals can serve as motivation for next season as they look to revive their fortunes under Gareth Ainsworth.

It's the time of year when the EFL play-offs – the most exciting domestic football competition in the world – takes centre stage, but it's been a while since Gillingham were involved.

The Kent club ended the 2024-25 season languishing in 17th in League Two, 10 places and 12 points adrift of the play-off places. And, while the dramatic action plays out to determine which of the teams finishing fourth to seventh will earn promotion to League One, Gills fans' thoughts can't help but turn to the three play-off campaigns that resulted in a trio of dramatic Wembley play-off finals for the Kent club.

Heartbreak at the old Wembley

Gillingham 2-2 Manchester City (AET, City win 3-1 on penalties), 1999

Gillingham's rough, tough brand of football helped them to a memorable campaign that saw them battle better-funded opposition to earn a spot in the 1999 Second Division play-off final, where they faced Manchester City.

The story heading into the game was all about City, the big club who had fallen on hard times, but the Gills had the most lethal strikeforce in the division in the form of Robert Taylor and Carl Asaba, who hit 16 and 20 league goals that season, respectively.

The game was a tense, tight affair with chances at a premium, but when Asaba burst through the City defence and slammed a shot past Nicky Weaver to put Gillingham up with just nine minutes to go, it looked like it would be the Kent club's day.

The celebrations in the Gills end turned to euphoria when Asaba and Taylor combined to put Gillingham 2-0 up. Asaba collected the ball, then brilliantly back-heeled the ball through for the charging Taylor, who fired low past Weaver. Gillingham were ahead with just three minutes remaining.

But when referee Mark Halsey for adding five minutes of stoppage time (during an era when five minutes of stoppage time was a rarity), City had a lifeline. Kevin Horlock netted as the clock hit 90, then Paul Dickov broke Gillingham hearts and become a City cult hero when he smashed high past Gills' keeper – and his best man at his wedding – Vince Bartram to score arguably the most important goal in City history.

After a nerve-shredding period of extra time, the match went to penalties, and Weaver saved twice from Paul Smith and Guy Butters either side of Adrian Pennock's miss to send City up and crush Gillingham hearts.

The agonising manner of that defeat lingered long in the memory, and served as motivation the following season as the Gills found themselves at the famous old stadium once again.

St. Thommo's Day

Gillingham 3-2 Wigan Athletic (AET), 2000

After losing out to City at Wembley the previous season, Gillingham were determined to put things right the following season and, under new manager Peter Taylor, the Gills took time to find their feet, but came good in the second half of the season.

The heartbreak returned on the final day of the season as a 1-0 away defeat at Wrexham cost the Kent side automatic promotion and sent them into the play-offs once again. But this time they simply refused to let history repeat itself.

After a come-from-behind semi-final win over Stoke, Gillingham found themselves at Wembley again, where they faced Wigan Athletic, a side that had received significant investment from then-owner Dave Whelan.

A 35th-minute Iffy Onuora goal (that some gave as a Pat McGibbon own goal) that JUST crossed the line put the Gills in front, only for a piece of Wembley brilliance from Wigan striker Simon Haworth to draw the Latics level on 59 minutes.

The tension rose as extra-time loomed, and Wigan fullback Kevin Sharp's sending-off with four minutes to go appeared to hand the Gills the advantage. But, in a dramatic twist, it was Wigan who took control in extra time when Barry Ashby was adjudged to have pulled down Darren Sheridan in the box and Stuart Barlow slammed home the spot-kick.

It looked like more Wembley heartbreak for the Gills, until a pair of substitutes produced a pair of unforgettable headers to give Gills fans the biggest moment in the club's history.

With six minutes left, first veteran striker Steve Butler, who was also part of Taylor's coaching staff, planted a header into the top corner from Junior Lewis' cross. Then, with just two minutes to go, Ty Gooden's cross – "a good 'un," according to Sky commentator Rob Hawthorne – was met by a spectacular diving header by super-sub Andy Thomson.

The ball flew into the bottom corner and 50,000 fans from Kent collectively lost their minds as the Gills snatched victory from the jaws of defeat and earned promotion to the Championship for the first time in the club's history.

That goal also remains the most euphoric moment in the history of Gillingham Football Club.

Simeon Jackson's late show

Gillingham 1-0 Shrewsbury Town, 2009

After Gillingham's relegation from the Championship in 2005, the club failed to recover and were relegated again three seasons later. But the 2008-09 season saw the Gills bounce back.

The club finished fifth in League Two to earn a spot in the play-offs, and ended up at the new Wembley for the first time as they faced Shrewsbury Town, a side who finished six points behind them during the regular season.

The match was one to forget, with chances few and far between. The importance of securing promotion seemed to weigh heavily on both sets of players, and it resulted in a less-than-memorable game.

But goals change games, and the moment that decided it came straight out of the EFL play-off drama playbook.

As the 90th minute ticked down, winger Andy Barcham earned a corner that, in truth, should have been given as a goal kick. It was a gift, a last-gasp chance at finishing the job before the drama of extra time and, possibly, penalties.

And when the corner was swung into the box, Gillingham's top scorer, Simeon Jackson, met it with a superb header that went in off the post to send the Gills fans behind the goal into delirium.

It was the ultimate sucker-punch goal, and one that saw Mark Stimson's Gillingham side earn promotion back to League One.

Play-off success can inspire Gills in 2025-26

Those play-off wins seem like a long time ago for Gillingham, and while the club did earn automatic promotion from League Two when Martin Allen's side won the title in 2012-13, but it's been more than a decade since Gillingham have celebrated promotion.

The club's owner, Brad Galinson, has dreams of delivering another promotion to the club, but after two and a half turbulent seasons that have seen multiple managerial changes, the club has struggled to deliver consistently on the pitch.

But now, under new boss Gareth Ainsworth, hopes are high that Gillingham can start looking up, rather than down, next season. A strong summer and a consistent season could put the Gills in position to challenge at the right end of the table, and finally rouse the "Sleeping Giant" that has laid dormant in Kent for more than a decade.