Woking v Southend United

Three successive victories had given Kieron Dyer an excellent start to life in charge of The Shrimpers, but Friday night’s 3-1 defeat at Roots Hall provided the first setback of the campaign.

The scoreline did not tell the whole story.

Southend had dominated much of the first half and led through Leon Chambers-Parillon’s tenth-minute goal, but a failure to turn that superiority into a more substantial advantage left the door open.

Kidderminster walked through it.

A Darren Oldaker own goal levelled the scores on the hour before Lewis Walker put the visitors ahead and Callum Stewart completed the turnaround in stoppage time.

Less than 72 hours later, there is an opportunity to respond.

And Woking have reasons of their own for wanting a reaction.

A Quick Chance To Put Friday Right

The nature of the Bank Holiday schedule means there has been very little time for Southend to dwell on their first defeat.

That may not be a bad thing.

There were enough positives in Friday’s opening 45 minutes to suggest The Shrimpers do not suddenly need to reinvent themselves.

The intensity was good.

Southend won possession high up the pitch, created opportunities and spent long periods in control.

What they didn’t do was finish the job.

The second half then provided a rather different test as Kidderminster’s substitutions changed the contest and Southend were unable to regain the authority they had enjoyed before the interval.

After winning their opening three matches against Altrincham, Scunthorpe United and Solihull Moors, Dyer now gets to see something new from his squad.

How do they respond to losing?

We won’t have to wait long to find out.

Woking’s Difficult Start

Woking also arrive at Monday’s fixture on the back of a defeat.

The Cards have taken three points from their opening four National League matches, scoring three goals and conceding eight.

Their campaign began with a difficult afternoon at the Laithwaite Community Stadium as Sutton United left with a convincing 3-0 victory.

Things didn’t improve on the first away trip.

Woking travelled to Gateshead and were beaten 2-0, leaving them without a point or a goal from their opening two fixtures.

Then came one of those matches capable of changing the mood around a club.

A Remarkable First Victory

AFC Fylde visited Woking on 22 August and twice took the lead.

Danny Ormerod put the visitors ahead during the first half before Matthew Ward capitalised on a defensive mistake to bring Woking level after the interval.

Fylde responded quickly through Harvey Broad.

With the game entering its final moments, Woking were heading towards a third successive defeat.

Instead, the afternoon was completely transformed.

Roy Syla thumped home an equaliser in the 90th minute before Taylan Harris struck in added time to complete a remarkable 3-2 comeback.

From no points to three in a matter of minutes.

It demonstrated that this is a Woking side capable of staying in a game even when circumstances appear to be against them.

That is something Southend will be particularly aware of after what happened against Kidderminster.

Hornchurch Bring Woking Back Down

Any hope that the dramatic victory over Fylde would immediately kick-start Woking’s season was checked on Friday night.

The Cards travelled to Hornchurch and were beaten 1-0, with Aaron Rowe scoring the decisive goal in the 74th minute.

Woking had opportunities to respond but couldn’t find an equaliser.

It leaves them with a simple opening record:

Southend will be determined to make sure Monday isn’t the afternoon that changes.

The Jermain Defoe Era

One of the most recognisable names in the National League is currently occupying the Woking dugout.

Jermain Defoe was appointed first-team manager on 29 March 2026, with the former England, Tottenham Hotspur, West Ham United and Sunderland striker moving into senior management following coaching experience at Tottenham and Rangers.

Defoe inherited the closing stages of Woking’s 2025/26 campaign and took charge of his first match against Eastleigh on 3 April, a 3-3 draw.

His first six games ultimately ended with Woking finishing the season in tenth place.

The new campaign therefore represents the first opportunity for Defoe to put his own stamp on the Cards over a full season.

The opening weeks have been difficult, but that dramatic win over Fylde has already demonstrated there is resilience within his side.

The Cards

Woking Football Club were formed in 1887 and take their nickname, the Cards, from the cardinal red used in the club’s traditional red and white colours.

Their history stretches across more than a century of non-League football.

There was even a point when one of English football’s biggest competitions may have helped ensure Woking continued to have a history at all.

In 1908, with the club facing serious financial difficulties, Woking battled through five qualifying rounds of the FA Cup to earn a First Round tie away to Bolton Wanderers.

Bolton won 5-0, but Woking’s achievement attracted national attention.

Impressed by their opponents, Bolton travelled to Woking for a friendly the following season, providing financial assistance at a crucial moment for the club.

It was an early chapter in what would become a particularly rich cup history.

Wembley, FA Cup Folklore And The Glory Years

Woking joined the Isthmian League in 1911 and remained in its top division for 72 years.

One of their greatest early achievements arrived in 1958.

In front of around 71,000 spectators, the Cards defeated Ilford 3-0 at Wembley to win the FA Amateur Cup.

But arguably the most famous result in Woking history came more than three decades later.

During the 1990/91 FA Cup, Woking fought their way through qualifying and three Conference opponents before travelling to First Division West Bromwich Albion in the Third Round.

They fell behind.

Then came the response.

Tim Buzaglo scored a famous hat-trick as Woking stunned Albion 4-2 at The Hawthorns.

Everton awaited in the Fourth Round.

The tie was switched to Goodison Park and Woking pushed a side packed with top-flight internationals all the way before Kevin Sheedy’s solitary goal ended the adventure.

By then, something special was developing at the club.

Three Trips To Wembley, Three FA Trophies

Under Geoff Chapple, Woking were promoted to the Conference in 1992.

The arrival of former Chelsea winger Clive Walker then helped inspire the most successful period in the club’s history.

Woking won the FA Trophy in 1994, 1995 and 1997, a haul which remains a joint record in the competition.

They also finished runners-up in the Conference in consecutive seasons, 1994/95 and 1995/96, while establishing themselves as one of the leading clubs in non-League football.

More FA Cup memories followed.

Millwall and Cambridge United were beaten during the 1996/97 competition before Premier League Coventry City narrowly escaped an upset.

Steve Thompson’s last-gasp equaliser at Highfield Road earned Woking a replay before Coventry eventually prevailed 2-1.

For supporters who remember non-League football during the 1990s, Woking were one of its defining clubs.

Relegation And The Road Back

Success became harder to sustain.

After 17 years at the highest level of non-League football, Woking were relegated in 2009.

They initially came close to an immediate return, reaching the Conference South play-off final in 2010 before losing to Bath City.

Garry Hill eventually delivered promotion in 2011/12, with Woking winning the division by nine points after losing just five league matches all season.

Another relegation followed in 2018, but the Cards again responded quickly.

Alan Dowson guided Woking through the National League South play-offs in 2019, defeating Welling United in the final and returning the club to the National League.

They have remained at this level ever since.

A Fixture That Doesn’t Like Producing Winners

If recent history is anything to go by, separating Southend and Woking on Monday could be difficult.

The six most recent meetings are:

That’s five consecutive draws between the clubs.

The last side to win this fixture?

Southend United.

The Shrimpers’ 2-0 victory at Woking in October 2023 remains the most recent decisive result between the teams.

Since then there have been three score draws and two goalless stalemates.

Perhaps Bank Holiday Monday will finally produce another winner.

What To Expect

The opening results suggest two sides arriving with rather different strengths and problems.

Southend have already shown they can score goals.

The Shrimpers hit three at Altrincham, found the winner against Scunthorpe, scored another three at Solihull and created more than enough opportunities to have built a commanding first-half lead against Kidderminster.

Woking’s problem has been finding the net consistently.

Three of their four league matches have ended without a Woking goal.

But dismissing the Cards on that basis would be dangerous.

Against Fylde they demonstrated how quickly a game can turn, scoring twice at the death to transform defeat into victory.

Southend hardly need reminding of that lesson.

Friday night provided one.