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Woking v Southend United: a quick chance to put Friday behind us

The first defeat has arrived. Bank Holiday Monday gives The Shrimpers an immediate opportunity to show how they respond.

Woking v Southend United match preview: both club badges and Shrimpie holding a half-and-half scarf.
THE MATCH AHEAD
DateMonday 31 August 2026
VenueLaithwaite Community Stadium
CompetitionEnterprise National League
Kick-off3pm
WokingvSouthend United

Well, the unbeaten start was enjoyable while it lasted. Now comes the important bit: how Southend respond.

Friday’s 3–1 home defeat by Kidderminster was a horrible way to end a run of three victories, especially after we had led from the tenth minute. Bank Holiday Monday gives Kieron Dyer’s side little time to dwell on it. We travel to Woking for a 3pm kick-off, looking to show that the first setback won’t define our opening month.

I don’t want to hear excuses about the short turnaround. Both clubs have had a Friday night match, and both will have tired legs. We have good players, we have nine points already and we have an opportunity to put things right.

What happened on Friday cannot become a habit

We played some decent football in the first half against Kidderminster. Leon Chambers-Parillon took his goal well, Ryan Colclough was lively and we created enough chances to be looking at a far more comfortable evening by the interval.

But we scored once, Kidderminster changed things after half-time and suddenly we seemed short of answers. A deflection brought them level, and then Lewis Walker and Callum Stewart completed a deserved comeback. It was an expensive lesson in what happens when a good spell isn’t turned into a commanding lead.

I don’t expect perfection after four games under a new manager. But I do expect the players to recognise when the opposition is getting on top and do something about it. A sensible pass, a won challenge, a change of tempo. Something that makes the other team work for the next five minutes.

Dyer has had three wins and a defeat to see different sides of his squad. This is the sort of match that tells a manager who is prepared to respond when things get uncomfortable.

Woking have had their own difficult start

Jermain Defoe’s Woking have three points from their opening four National League games. They lost to Sutton United and Gateshead, fought back for a dramatic 3–2 home victory against AFC Fylde, then were beaten 1–0 at Hornchurch on Friday.

Three points from four isn’t where they will want to be, but the Fylde match is worth a closer look. Woking were staring at defeat late on before Roy Syla equalised and Taylan Harris found a winner. Those last-minute goals gave their supporters proof that the side is capable of fighting to the very end.

After Hornchurch, the Cards will be looking to make a statement in front of their own crowd. They are not likely to sit back and politely allow us to recover from the Kidderminster disappointment.

Southend supporters know all about the expectations that come with a new manager. Defoe brings a huge playing reputation to Woking, while Dyer has his own experience at the highest level. But the reputations on the touchline will count for very little once this match begins. It will come down to decisions, movement and the players prepared to do the difficult work.

Opposition player to watch: Roy Syla

Roy Syla is the Woking player I’d be especially wary of. The midfielder scored the late equaliser against Fylde that started their remarkable comeback, and he can carry the ball into areas where defenders suddenly have an extra problem to deal with.

He wears number eight and will want to dictate the pace when Woking have the ball. If Southend allow him too much room to turn and run at our back line, we could make another away afternoon harder than it needs to be.

Syla is not the only threat. Taylan Harris showed the value of persistence by grabbing that winner against Fylde, and Woking have options in the forward positions. We need to be first to loose balls, stay switched on around the edge of the box and be ready for the home side to have their own dangerous spells.

It’s worth remembering how often these clubs have been hard to separate in recent meetings. Draws have become rather familiar. I’d love to see us repeat the 2–0 victory we enjoyed here in October 2023, but nothing from three years ago will win the match for the current team.

Who gets the chance to respond?

There will be tired legs after Friday, and Dyer may well feel the need to make changes. The attacking options give him choices: Harry Cardwell’s work rate, Josh Popoola’s instinct around goal, Charley Kendall’s movement and the pace of Sahid Kamara all offer something different.

Ryan Colclough caused Kidderminster problems without finding the finish to match. Oli Coker has already influenced some important goals, while Chambers-Parillon is making himself difficult to leave out. There are places to fight for here, and that competition should be healthy.

What matters is the connection between midfield and attack. Too often on Friday we threatened to build a second goal, only for the move to end without a finish. We can’t rely on one moment of quality and then spend the afternoon protecting it.

At the other end, I want the defence to be given a platform. Joe Duncan has had to make some exceptional saves already this season. It’s comforting to have a goalkeeper who can do that, but it’s no way to build a consistent promotion challenge if he is left exposed week after week.

Monday offers a proper chance to reset

There is a temptation after a defeat to demand sweeping changes. I don’t think we’re at that stage. Three wins showed this team has character and the ability to score. Kidderminster showed how quickly a game can get away if we stop imposing ourselves. The answer is to learn from both.

Start positively, move the ball with purpose and don’t let Woking get comfortable. If we take the lead, keep playing; don’t treat it as an invitation to retreat. And if we go behind, we already know we have players capable of turning a scoreline around.

Show us Friday hurt

I’m still annoyed about the Kidderminster result. Not because I expected us to win every game, but because it was a match we had worked ourselves into a position to control. We should have made more of that first half.

What I want from Woking is not a frantic reaction. I want focus. Win the ball, support your teammates, use the attacking quality we know is there and make sensible decisions when Woking have their moment.

A fourth victory would send us into September with twelve points from fifteen, and I’d happily take that. But whatever the result, I want to finish the afternoon feeling that the players have taken Friday’s lesson seriously.

It’s a Bank Holiday away day, and our supporters will do their bit. Time for the team to do theirs. Up the Shrimpers.

THE FINAL WHISTLE ISN’T THE LAST WORD.

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