My 25 worst Portsmouth games in 25 years at The News: From Bootham Crescent to Rodney Parade, Etihad to Globe Arena

Chief sports writer Neil Allen this month has toasted 25 years at The News - and takes a look at his worst Pompey matches covered.

To mark the 25th anniversary of my November 2000 arrival at The News, I listed my top-25 favourite Pompey matches covered.

So now it’s time for the worst matches covered...

25) Chelsea 1 Pompey 0 - FA Cup final - May 2010

I appreciate not all will agree, yet it was the nonsense off the pitch for the Wembley final which really irritated me.

With Pompey in administration, I was appalled to see smiling nemesis Balram Chainrai sitting alongside Prince William in the Royal Box. Likewise, his son being one of the mascots really stuck in my throat. Still, every time Chainrai senior was flashed up on the big screen, he was greeted with boos.

Heartbreak for Ricardo Rocha following defeat to Chelsea in the 2010 FA Cup final. Picture: Steve Reidplaceholder image
Heartbreak for Ricardo Rocha following defeat to Chelsea in the 2010 FA Cup final. Picture: Steve Reid | Steve Reid

Anyhow, in the aftermath, Chainrai’s lawyer emailed The News of their intent to sue over my match report in which I criticised him - and other owners - for their part in the Blues’ financial demise.

As a consequence, the report was removed online. Despite the threat, however, he never followed through.

24) Plymouth 3 Pompey 0 - League Cup - August 2012

With Pompey still in administration and under a registration embargo, Michael Appleton fielded a team consisting of nine teenagers, his assistant manager and goalkeeper Simon Eastwood.

Meanwhile, Balram Chainrai was hanging around saying he wanted the club yet again. Upon arriving at Home Park, it was clear misinformation was being put out about the situation, painting Uncle Balu in a positive light. So, after speaking to the Trust and administrator Trevor Birch before the game to get the actual facts, I put the record straight at half-time during an Express FM chat with Mark Mudie.

Admittedly, I also called upon Chainrai to ‘clear off’ - prompting an unhappy Express FM to cut me off early, from their Portsmouth studio.

I returned to the press box with 89 Tweets congratulating my outburst and one having a real go at my ‘lack of professionalism’. Some could never see any wrong in Balram Chainrai.

23) AFC Wimbledon 4 Pompey 0 - November 2013

Pompey’s first encounter with AFC Wimbledon took place at the Cherry Red Records Stadium - and ended in a hammering which contributed to boss Guy Whittingham losing his job after the following match.

The Blues conceding three goals in the final 16 minutes as they slumped to a 4-0 defeat at AFC Wimbledon. Picture: Joe Peplerplaceholder image
The Blues conceding three goals in the final 16 minutes as they slumped to a 4-0 defeat at AFC Wimbledon. Picture: Joe Pepler

The Blues had lost at Stevenage and Newport County in the previous two games and this completed a wretched hat-trick of shocking performances on the road.

Pompey were so bad, a furious chairman Iain McInnes left his directors’ box seat with eight minutes remaining, never to return. He later claimed he needed the toilet rather than storming off. Perhaps he was throwing up.

22) Manchester City 6 Pompey 0 - September 2008

This was Pompey at the peak of their Premier League powers, with Harry Redknapp as manager and a team which had triumphed in the FA Cup and finished eighth just four months later.

Yet, inexplicably, they were blown away by a Manchester City side who weren’t even that good, ultimately finishing 10th that season, 40 points adrift of eventual Premier League winners Manchester United.

In fact, on the same day, the takeover by the Abu Dhabi United Group was announced - taking them to a whole new level, but obviously after this game.

Incidentally, Pompey’s starting XI contained David James, Glen Johnson, Sylvain Distin, Sol Campbell, Lassana Diarra, Peter Crouch and Jermain Defoe. Weird.

21) Oxford United 1 Pompey 1 - 5-4 on penalties - League One Play-Off Semi-final Second Leg - July 2020

The League One season had resumed following Covid, yet only in the form of the play-offs - and to be played behind closed doors.

Cameron McGeehan (far right) missed a Pompey penalty against Oxford United in July 2020. Picture: Robin Jones/Getty Imagesplaceholder image
Cameron McGeehan (far right) missed a Pompey penalty against Oxford United in July 2020. Picture: Robin Jones/Getty Images

Following a 1-1 Fratton Park draw, the teams headed to the Kassam Stadium and Marcus Harness gave Pompey the lead, only for Ellis Harrison’s headed own goal to level on the stroke of half-time.

The tie finished 2-2 on aggregate, with a penalty shoot-out now deciding the winners. However, Cameron McGeehan missed and it was Oxford who progressed to the final. For Pompey, it was a League One semi-final play-off defeat in successive seasons.

20) Pompey 2 Peterborough 3 - April 2019

Third-placed Pompey were four points adrift of the promotion spots - but had a game in hand heading into the final week of the League One season. This was a must-win.

It was 2-2 after 73 minutes, then Brett Pitman galloped down the right with just the keeper to beat and unselfishly opted to square a pass to Viv Solomon-Otabor, who gleefully turned it into the net.

Viv Solomon-Otabor’s goal was ruled out for off-side - and minutes later Ivan Toney grabbed the winner for Peterborough. Picture: Robin Jones.placeholder image
Viv Solomon-Otabor’s goal was ruled out for off-side - and minutes later Ivan Toney grabbed the winner for Peterborough. Picture: Robin Jones.

But wait, the Birmingham loanee had been correctly flagged offside - and moments later Ivan Toney grabbed what would prove to be the winner for the Posh. Heartbreaking.

19) Swindon 5 Pompey 0 - New Year’s Day 2013

In administration, without a permanent manager, languishing 21st in League One and facing the possibility of liquidation, Pompey were already on their knees for the trip to Swindon.

Substitute James Collins scored a 12-minute hat-trick and finished with four goals overall as the Robins ran riot against Pompey. Picture: Sarah Standingplaceholder image
Substitute James Collins scored a 12-minute hat-trick and finished with four goals overall as the Robins ran riot against Pompey. Picture: Sarah Standing

To their credit, it was goalless against Paolo Di Canio’s until the 61st minute - then the Robins scored four goals in a wretched 12-minute spell. In fact, substitute James Collins helped himself to four overall in the 5-0 win for the hosts.

Di Canio couldn’t have been that happy, mind. He smashed the perspex glass in Swindon’s dugout at one point.

18) Pompey 0 Crewe 1 - March 2017

Paul Cook’s fourth-placed side were pushing for promotion from League Two with struggling Crewe the latest club to visit Fratton Park.

The Railwaymen had won two of their previous 16 league games and were languishing in 20th place - and you can guess the rest. George Ray’s 77th-minute goal earned the visitors a shock 1-0 win amid an unpleasant atmosphere, particularly towards Cook.

A dismal home defeat to Crewe saw some fans turn on Paul Cook and also the manager questioning his own future. Picture: Joe Peplerplaceholder image
A dismal home defeat to Crewe saw some fans turn on Paul Cook and also the manager questioning his own future. Picture: Joe Pepler

One fan by the dugout could be heard berating the manager afterwards, demanding for his sacking, with others no doubt in agreement. Indeed, chief executive Mark Catlin and some of the players feared he would subsequently hand in his notice.

Thankful Pompey lost one of their next 12 matches to win the League Two title - with Cook at the helm.

17) Newport County 3 Pompey 0 - Johnston Paint Trophy - November 2013

Guy Whittingham’s Pompey turned in a shocker of a display, particularly Joe Devera in the home defence, as they slumped to a 3-0 defeat at Newport County.

The visitors were abject, falling 2-0 behind after 19 minutes through some horrendous defending, and never looked likely of finding a way back, even when the Exiles were reduced to 10 men with David Pipe given his marching orders with 22 minutes remaining.

In fact, Justin Edinburgh’s man would grab a third in the 83rd minute to sum up a shocking evening for the Blues.

16) Pompey 0 Accrington 1 - May 2021

The Blues occupied the final League One play-off spot heading into the last match of the season against Accrington Stanley at Fratton Park after rallying under Kenny Jackett’s replacement Danny Cowley.

Dejected Pompey skipper Tom Naylor following the 1-0 home defeat to Accrington in May 2021.placeholder image
Dejected Pompey skipper Tom Naylor following the 1-0 home defeat to Accrington in May 2021.

One point ahead of rivals Oxford United and Charlton, it was in their hands. Cowley sprang a surprise before kick-off by dropping Sean Raggett, ending his ever-present league record, but further shocks were to come, with Adam Phillips’ first-half strike earning the visitors victory.

With Oxford and Charlton both winning, the Blues ultimately finished eighth, missing out by two points. Then the players went out for end-of-season drinks in Southsea and some ended up being barred from Astoria. Ignore the grapevine, it wasn’t Ronan Curtis either.

15) York 4 Pompey 2 - September 2013

John Sullivan’s Pompey career will always be synonymous with one game - sadly, for all the wrong reasons.

The former Charlton goalkeeper was part of Guy Whittingham’s huge summer recruitment drive after the Blues had been saved from liquidation at the High Court, yet his career on the south coast effectively ended that very afternoon.

John Sullivan endured a nightmare match, including conceding three goals in eight minutes, at York. Picture: Joe Peplerplaceholder image
John Sullivan endured a nightmare match, including conceding three goals in eight minutes, at York. Picture: Joe Pepler

It began in the fourth minute when Sullivan spilled a free-kick which was finished from close range and, from that point, the likeable stopper put in a shocking performance, crumbling in front of our very eyes.

By rights, we should have been talking about Jed Wallace’s second-half wonder goal, but it will always be the John Sullivan game.

14) Stoke 6 Pompey 1 - October 2024

The game was finely poised at 1-1 heading into half-time - then it was carnage as John Mousinho’s men spectacularly imploded.

Stoke netted five times in 10 minutes, with half-time in the middle of it, as loanee Tom Cannon bagged four of them, leaving the Blues shell-shocked and 23rd in the Championship.

It's agony for Mark O'Mahony and his Pompey team-mates after a 6-1 hammering at Stoke. Picture: Jason Brown/ProSportsImagesplaceholder image
It's agony for Mark O'Mahony and his Pompey team-mates after a 6-1 hammering at Stoke. Picture: Jason Brown/ProSportsImages | Jason Brown/ProSportsImages

League One title-winning keeper Will Norris never played for the club again, while full debutant Harvey Blair disappeared until the final month of the season.

13) Pompey 3 Coventry 3 - August 2019

Kenny Jackett’s side were 3-1 up and cruising after 75 minutes against a Coventry side reduced to 10 men following Fankaty Dabo’s sending off.

Matt Godden pulled one back to make it 3-2, only for the visitors to immediately go down to nine men after Gervane Kastaneer was also given his marching orders.

Pompey appeared to be cruising to a 3-1 victory over 10-man Coventry with 15 minutes remaining. It ended 3-3. Picture: Robin Jones/Digital Southplaceholder image
Pompey appeared to be cruising to a 3-1 victory over 10-man Coventry with 15 minutes remaining. It ended 3-3. Picture: Robin Jones/Digital South

Fearing the danger posed by a side losing 3-2 away from home and having two fewer players, Jackett replaced Gareth Evans with centre-half Christian Burgess as he attempted to shut up shop.

Then Michael Rose netted four minutes from time and the nine-man Sky Blues had completed a sensational comeback. While Jackett never regained the confidence of some members of the Fratton faithful.

12) Hartlepool 0 Pompey 0 - February 2013

The original League One fixture at Hartlepool was postponed earlier in the season due to a waterlogged pitch, so it was rearranged - for a Tuesday night.

If embarking on a 646-mile journey midweek wasn’t bad enough for the incredible Fratton faithful, Guy Whittingham’s men headed there on the back of nine successive defeats.

So in one respect, a point collected on a bitterly cold evening at Victoria Park was a moral victory - although still set a new club record of 20 games with a win.

11) Northampton 4 Pompey 1 - March 2021

Kenny Jackett’s fifth-placed side ventured to Sixfields for a behind-closed doors League One fixture - and found themselves 4-0 down at half-time to a side struggling against relegation.

The performance really was as bad as the scoreline suggests as Pompey but in an absolutely shocking display, arguably the worst of Jackett’s era, certainly in the league.

Bafflingly, he didn’t even make any substitutions at the break, instead waiting until the 59th minute before hauling off four members of that shambolic side. One of those who came off the bench was Ellis Harrison, who grabbed a consolation 17 minutes from time through a penalty.

In one of the worst performances of the Kenny Jackett era, the Blues found themselves 4-0 down after 43 minutes in the behind-closed-doors trip to struggling Northampton. Picture: Pete Norton/Getty Images.placeholder image
In one of the worst performances of the Kenny Jackett era, the Blues found themselves 4-0 down after 43 minutes in the behind-closed-doors trip to struggling Northampton. Picture: Pete Norton/Getty Images.

The writing was on the wall for Jackett - he was dismissed two matches later following losses to Sunderland and, in the EFL Trophy final, Salford.

10) Pompey 0 Sunderland 0 - League One Play-Off Second Leg - May 2019

Kenny Jackett’s men had returned from the Stadium of Light with a 1-0 first-leg deficit, although still leaving them in a decent position considering the deciding leg was at Fratton Park.

So it was all teed up for a fascinating evening under the lights against Sunderland - and absolutely nothing happened. Sunderland were happy to dig in for their lead and Pompey were lethargic and lacked any sort of attacking impetus.

It was immensely frustrating, the game was effectively over early in the second half as it petered out into a drab goalless draw, much to the disbelief of the Fratton faithful.

To add to the anger, leading scorer Jamal Lowe and Ronan Curtis had been named on the bench, with the latter bizarrely unused, despite Jackett not using up all his substitutions.

Pompey were eliminated - and it also cost them Lowe and Matt Clarke, who moved to Wigan and Brighton respectively for big transfer fees.

9) Pompey 0 Salford 0 - 2-4 on penalties - EFL Trophy Final - March 2021

The Covid outbreak meant the 2020 Wembley final had to be played a year later than initially scheduled - and behind closed doors.

Had it not been for Craig MacGillivray’s goalkeeping masterclass, Kenny Jackett’s men wouldn’t have even got to penalties, as they were embarrassed by mid-table League Two opposition.

Pompey lost on penalties to Salford in the EFL Trophy final in March 2021. Picture: Habibur Rahmanplaceholder image
Pompey lost on penalties to Salford in the EFL Trophy final in March 2021. Picture: Habibur Rahman

Ultimately, Ryan Williams and Ronan Curtis missed their spot-kicks and it was Salford who claimed the trophy, with the underdogs triumphing. Deservedly too.

The following day, Jackett was sacked as Pompey manager after three-and-a-half years in the job.

8) Plymouth 3 Pompey 0 - November 2014

Positioned 13th in League Two, Pompey were without an away win in six matches when they headed to Home Park for the televised fixture. Manager Andy Awford’s solution was to name a central midfield consisting of his son Nick and Jack Whatmough.

Andy Awford's controversial decision to hand son Nick a full debut in the centre of midfield in the televised clash at Plymouth backfired. Picture: Joe Peplerplaceholder image
Andy Awford's controversial decision to hand son Nick a full debut in the centre of midfield in the televised clash at Plymouth backfired. Picture: Joe Pepler

Furious chairman Iain McInnes later insisted he asked his manager whether he was ‘out of his mind’ when told of the selection the previous night - and his mood was considerably worse after the subsequent defeat.

The Blues were 3-0 down after 30 minutes during a dreadful first half and Awford junior never played for the club again.

7) York 3 Pompey 1 - April 2016

I hated Bootham Crescent, the worst Football League ground I’ve ever seen Pompey play at. The desks in the press box were missing, although the frame remained, so you sat with the laptop in your lap and the team sheet placed on the terrace steps next to you.

In fact, I hated Bootham Crescent long before the 3-1 defeat under Paul Cook which effectively ended hopes of automatic promotion in his first season in charge.

York were 3-0 up after 48 minutes, yet even that shock win couldn’t save their Football League future. They finished bottom a month later and have been in non-league ever since.

6) Plymouth 1 Pompey 0 - League Two Play-Offs Second Leg - May 2016

The tie was fascinatingly poised at 2-2 following the Fratton Park first leg, yet, crucially, Paul Cook’s side was devastated by injury. Matt Clarke, Adam Webster. Paul Jones, Kieron Freeman and Brian Murphy were all ruled out. Then Gareth Evans and Danny Hollands were forced off in the first half and ended up on crutches.

Pompey suffered a last-gasp defeat at Plymouth in May 2016 to be eliminated from the League Two Play-Off semi-finals. Picture: Joe Peplerplaceholder image
Pompey suffered a last-gasp defeat at Plymouth in May 2016 to be eliminated from the League Two Play-Off semi-finals. Picture: Joe Pepler

To make matters worse, Michael Doyle, Conor Chaplin and Enda Stevens played on through injuries, while Ben Davies shrugged off concussion sustained in the game to continue.

Heartbreakingly, Plymouth’s Peter Hartley scored a 90th-minute winner, sparking a pitch invasion from celebrating home supporters. One of their gloating number also entered the then-enclosed press box to dance and yawp in front of us, which was lovely.

5) Morecambe 1 Pompey 1 - February 2016

Barry Roche - some of us will never forget the name. You don’t see many goalkeepers scoring 94th-minute headers from corners. We did that night.

Paul Cook’s side looked set for victory through Gareth Evans’ first-half goal, then the hosts’ veteran goalkeeper grabbed a stoppage-time leveller in a remarkable finale.

Morecambe goalkeeper Barry Roche headed home a 94th-minute corner to claim a point against Pompey. Picture: Joe Peplerplaceholder image
Morecambe goalkeeper Barry Roche headed home a 94th-minute corner to claim a point against Pompey. Picture: Joe Pepler

Morecambe’s PA announcer was so delighted, he jumped on my desk and started dancing beside me as I attempted to swiftly rewrite my match report. Barry Roche.

4) Pompey 2 Crystal Palace 4 - May 2001

Palace won on an angry Fratton Park evening to leap over Graham Rix’s side and shove them into the Division One relegation zone with one game to play.

Indeed, the visitors were 4-1 up after 51 minutes and the atmosphere around the ground was absolutely toxic, with a season ticket thrown in front of Lee Bradbury at one point as supporters vented their thoughts.

In Played Up Pompey 3, Gary O’Neil revealed how he was on the right-hand side of midfield that night and tried to keep away from the North Stand touchline, fearing his own fans!

3) Pompey 1 Oxford United 4 - August 2013

The dawning of a new era under fan ownership was marked with the iconic sight of ‘Ours’ being spelt by cards held up in the Fratton End pre-match.

On a gloriously sunny day, it was also the perfect start for Guy Whittingham’s men, with Patrick Agyemang opening the scoring after 25 minutes. Then everything turned.

An iconic image against Oxford, but Pompey lost 4-1 on the big day. Picture: Joe Peplerplaceholder image
An iconic image against Oxford, but Pompey lost 4-1 on the big day. Picture: Joe Pepler

By the time Pompey were reduced to 10 men after skipper Johnny Ertl elbowed future Blues player Danny Rose in the head, they were trailing 3-1 - and there was to be no coming back.

Talk about ruining the big occasion, yet it proved to be no one-off in a season which saw Pompey threatened with relegation to the non-league.

2) Aldershot 1 Pompey 0 - FA Cup - November 2014

Danny Hollands had levelled nine minutes from time to prevent the non-leaguers winning at Fratton Park. Now the sides had to meet once more in the replay.

Pompey suffered defeat to a non-league side in a cup competition for the first time in their Football League history against Aldershot in November 2014. Picture: Joe Peplerplaceholder image
Pompey suffered defeat to a non-league side in a cup competition for the first time in their Football League history against Aldershot in November 2014. Picture: Joe Pepler

Incredibly, Andy Awford’s men were even worse at the Recreation Ground, with Mark Moseley netting in the 81st minute to inflict a huge cup shock on the League Two Blues.

To add to the humiliation, it was the first time in Pompey’s Football League history they had been beaten by a non-league team.

I distinctly remember that same evening having a Twitter argument with a Pompey fan chastising me for being too critical of the performance. Bizarre.

1) Pompey 1 Leyton Orient 4 - FA Cup - January 2002

Will always be my bar to judge the level of a bad Pompey performance. To this day, absolutely nothing comes close to that horrific FA Cup defeat at home to a Leyton Orient side from the division below.

The error-strewn Yoshi Kawaguchi was so bad, he never started for the club again and afterwards the keeper was in tears as he spoke to the sizeable Japanese press pack.

Pompey had taken the lead too. In fact, you’d have to ask how on earth a team containing the likes of Linvoy Primus, Scott Hiley, Robert Prosinecki, Nigel Quashie, Gary O’Neil, Kevin Harper and Peter Crouch managed to fall to such a wretched loss.

Under-pressure boss Graham Rix somehow survived - although Milan Mandaric’s axe instead fell on his assistant Jim Duffy 48 hours later. Apparently he wanted to spend more time with his family in Scotland. Of course he did.

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