Sheppey United vs Chertsey: Match Preview, Predictions and Betting Tips
Published on Thursday, 01 October 2026 by Steve
Sheppey United vs Chertsey Town
Emirates FA Cup - Third Qualifying Round Prediction & Betting Tips
Match Overview
Season 2019-20 - Sheppey United - SCEFL
There is something uniquely romantic about FA Cup qualifying weekend in October, and this third qualifying round tie between Sheppey United and Chertsey Town at the Sharrocks Stadium, Holm Park, captures it perfectly. Two community clubs separated by a single division but united by history - both were founded in 1890 - will battle on Saturday 3rd October 2026 (3pm kick-off) for a place in the fourth qualifying round, just one win away from the possibility of being paired with Football League opposition in the first round proper. For Sheppey, the memories of their historic 2023-24 run - the penalty shoot-out upset of Billericay Town and the televised glamour tie against Walsall - are still vivid around Halfway, and the Ites will fancy their chances of another deep run on home soil. Chertsey Town, the Curfews, arrive from Alwyns Lane as the nominal favourites from the division above, and our football predictions for today rate this as one of the most competitive non-league cup ties on the card. You can also find this fixture featured among our wider hot predictions for the weekend.
The form book leans towards the visitors, but only slightly. Chertsey finished seventh in the Southern League Premier Division South last season - securing their Step 3 status comfortably - and have carried that momentum into 2026/27, collecting ten points from their opening six league matches to sit among the early pace-setters. Manager Toby Little has added experienced winger Seb Bowerman to an attack already boasting the prolific Jack Mazzone, and the Curfews have won three of their last six away outings. Sheppey, by contrast, endured a difficult 2025-26 campaign that ended with an 18th-placed finish in the Isthmian League South East Division, but the green shoots of recovery are visible: back-to-back league victories, including a confidence-boosting win over Peacehaven & Telscombe, have transformed the mood at Holm Park heading into cup week. If you are building a weekend slip, our football predictions for tomorrow page tracks how the odds move on ties like this once team news drops.
Beyond pride and progress, there is serious money at stake. The winners of this tie will bank more than Β£5,000 in FA Cup prize money plus a share of the gate - vital income at Step 3 and Step 4 level - and will be just 90 minutes (plus, potentially, a replay) from the fourth qualifying round, where the competition begins to capture national attention. A draw after 90 minutes would send the tie to a replay at Alwyns Lane in midweek, a scenario neither side will welcome given congested league schedules. With tickets priced at Β£10 for adults, Β£5 concessions and under-15s admitted free, a healthy crowd is expected on the Isle of Sheppey to see whether the Ites can upset the odds or whether Chertsey's extra division of experience will prove decisive. Our full betting breakdown, including the correct score pick, is covered in detail below.
Tactical Preview
Jack Mazzone - Horsham Football Club
Formation & Key Matchups
Sheppey United 4-2-3-1
Joint managers George and Ian Batten have typically deployed the Ites in a compact 4-2-3-1 this season, prioritising structure and set-piece threat over sustained possession. At Holm Park - a big, exposed pitch where the wind whips in off the Thames estuary - Sheppey look to play direct into target man Dan Bradshaw, with Danny Leonard and Jacob Lambert tasked with winning second balls in the double pivot. The full-backs are encouraged to overlap when the home crowd gets behind them, which is precisely when the Ites are at their most dangerous but also at their most vulnerable.
Chertsey Town 4-2-3-1
Toby Little's Curfews mirror the shape but interpret it differently. Chertsey are far more comfortable circulating possession, with Ashley Lodge and Louis Birch screening in front of a settled back four captained by Alex Fisher. New signing Seb Bowerman provides genuine one-versus-one quality off either flank, while Jack Mazzone operates on the shoulder of the last defender, darting into the channels whenever the wide players attract a double-team. Chertsey's full-backs push high, and their front four interchange freely - a level of fluency you would expect from a side sitting one division higher.
Critical Vulnerability
The decisive zone will be the space behind Sheppey's advanced full-backs. When the Ites commit bodies forward at home, their double pivot is frequently dragged wide to cover, leaving the inside channels open. That is Mazzone's favourite hunting ground, and with Bowerman isolating a retreating full-back on the opposite side, Chertsey have the weapons to punish any over-commitment. Conversely, if Sheppey can keep the game tight for an hour, their set-piece delivery and the Holm Park atmosphere give them a genuine route to an upset - but defensive transitions are the clear vulnerability the Curfews will target.
Team News & Squad Status
Sheppey United ββͺββ β
- The Ites head into cup week on the back of back-to-back Isthmian South East league wins, including victory over Peacehaven & Telscombe, after a sluggish start to 2026/27.
- Aiden Prall is expected to continue in goal, having established himself as first choice at Holm Park.
- Lekan Majoyegbe and Mamadou Diallo are the preferred central defensive pairing, with academy graduates Ryan Freeman and Alfie Bates providing energy at full-back.
- Danny Leonard and Jacob Lambert anchor the midfield, with Dan Bradshaw leading the line as the focal point of the attack.
- No fresh suspensions reported; the club's youth-to-first-team pathway gives the Battens useful depth on a cup-allowance bench of seven.
Chertsey Town β βͺβ βͺββ
- The Curfews have taken 10 points from their opening six Southern Premier South fixtures and sit among the early pace-setters at Step 3.
- Summer signing Seb Bowerman - recruited from Farnham Town after six productive seasons with Bracknell Town - is pushing for a start on the flank.
- Jack Mazzone remains the talisman: the striker fired 30 goals in all competitions in his breakout campaign and is the man Sheppey must subdue.
- Alex Fisher captains the side from centre-back, with Luke Wynne Roberts between the posts and Isaac Olorunfemi at right-back.
- Player-manager Toby Little may use the FA Cup's seven-substitute rule to rotate, but is expected to name a strong XI given the prize money on offer.
Predicted Lineups
Sheppey United winger Danny Leonard on staying at Holm Park and rediscovering his best form after injury setback
| Sheppey United 4-2-3-1 | Chertsey Town 4-2-3-1 |
|---|---|
| GK: Aiden Prall | GK: Luke Wynne Roberts |
| RB: Ryan Freeman | RB: Isaac Olorunfemi |
| CB: Lekan Majoyegbe | CB: Alex Fisher (c) |
| CB: Mamadou Diallo | CB: Darryl Harrison |
| LB: Alfie Bates | LB: Eoin Casey |
| DM: Jacob Lambert | DM: Ashley Lodge |
| CM: Danny Leonard | CM: Louis Birch |
| RM: Kai Mason | AM: Toby Little |
| AM: Jordan Aina | RM: Seb Bowerman |
| LM: Kieran Harris | LM: Oliver McCoy |
| ST: Dan Bradshaw | ST: Jack Mazzone |
Head-to-Head Record
These two historic clubs have crossed paths only four times in the modern era, and the fixture has been dominated by the Curfews. The most eye-catching meeting came in September 2019, when Chertsey Town - then managed by Dave Anderson - thrashed Sheppey 4-1 at Alwyns Lane in FA Cup qualifying, a result that still stings on the Isle of Sheppey. The most recent encounter followed a similar pattern, Chertsey edging it 1-0, meaning the visitors arrive unbeaten in the last three meetings between the sides. Sheppey's only win in the sequence came in an Isthmian League fixture played several years earlier, and the Ites have never beaten Chertsey in the FA Cup.
The goals trend is just as telling: three of the four meetings have produced Over 2.5 goals, and both teams have found the net in three of the four as well. The 2019 tie alone produced five goals, and Chertsey's current vintage is arguably more potent than that side, with Mazzone and Bowerman offering a blend of penalty-box craft and wide creativity that Sheppey have struggled to contain historically. For bettors following the both teams to score markets, this fixture profile is extremely familiar - and for those who prefer totals, our over/under predictions highlight how rarely these two keep clean sheets against one another.
Key Players Comparison
Dan Bradshaw - Sheppey United
The Ites' focal point. Bradshaw's hold-up play and aerial presence give Sheppey an outlet when they are pinned back, and his movement across the front line will test Fisher and Harrison physically. If Sheppey are to spring a surprise, it will likely be Bradshaw applying the finish.
Danny Leonard - Sheppey United
The creative heartbeat. Leonard's delivery from set pieces and threaded passes from the double pivot are Sheppey's most reliable source of chances against organised defences - and Chertsey are nothing if not organised.
Jack Mazzone - Chertsey Town
The proven marksman. A 30-goal all-competitions season underlined Mazzone's status as one of the most feared forwards at Step 3. His movement between centre-back and full-back is exactly the weapon to exploit Sheppey's transitional weakness.
Seb Bowerman - Chertsey Town
The new wildcard. Recruited from Farnham Town after promotion-winning campaigns with Bracknell Town, Bowerman's ability to beat a man on either flank and arrive late in the box adds a dimension the Curfews lacked last season.
The individual battle maps neatly onto the team battle: Sheppey's route to goal runs through Bradshaw and Leonard's set-piece delivery, while Chertsey can hurt you from three or four different positions. That multiplicity of threats is why the visitors are odds-on favourites, but cup football has a habit of compressing talent gaps - particularly on a blustery afternoon in front of a partisan Holm Park crowd. Bradshaw against Fisher is the duel that could decide whether this tie becomes the tight, scrappy contest Sheppey need, or the open game Chertsey crave. Our sure win predictions team flags player-form mismatches like this one when assessing upset potential.
The Managers
George Batten & Ian Batten (Sheppey United)
Joint managers George and Ian Batten carry one of the most poignant remits in non-league football: continuing the work of their father, Ernie Batten, the club's greatest manager, who passed away in March 2025. Under the brothers' stewardship the Ites have remained competitive in the Isthmian South East while honouring the family's "Built From The Community For The Community" philosophy that transformed Sheppey from nomads into a stable, ambitious Step 4 club with a thriving academy pipeline.
Tactically the Battens are pragmatists. They organise compact mid-blocks, demand intensity in duels, and lean heavily on the Holm Park crowd - a factor that has produced famous cup nights against Billericay and Walsall in recent memory. Their challenge on Saturday is balancing that trademark defensive resilience with enough attacking ambition to test a side one division higher.
Toby Little (Chertsey Town)
Toby Little's path to the Chertsey dugout has been anything but conventional. The former Hayes & Yeading, Chesham United and Beaconsfield Town midfielder joined the Curfews as a player in 2023, transitioned into a player-coach role, and was thrust into the manager's seat in October 2025 after a mid-season change. The response was emphatic: a nine-game unbeaten run early in 2026 propelled Chertsey to a seventh-placed finish in the Southern Premier South and secured their Step 3 status.
Now fully in charge of the 2026/27 campaign - with Scott Donnelly, Dan Canning and new arrival Steve Baker alongside him - Little has stamped an assertive, front-foot identity on the Curfews. Ten points from six league games suggests genuine play-off aspirations, and the player-manager will be acutely aware that a Cup run both funds and accelerates that project.
Betting Predictions & Tips
Odds: 1.83
Chertsey are a division higher, arrive in strong early-season form, and hold a psychological edge having won the last three meetings between the clubs. Sheppey's improving form makes them dangerous, but the visitors' superior squad depth and attacking fluency should tell over 90 minutes. This selection also anchors our weekend bet of the day analysis, where the Curfews' away record (three wins in their last six on the road) is the deciding factor.
Odds: 3.30
Sheppey score regularly at Holm Park and both teams have found the net in three of the four head-to-head meetings, but keeping Chertsey's front four quiet is a different proposition entirely. Combining the away win with BTTS roughly doubles the value of the straight win while remaining well supported by the data - the 4-1 scoreline from the 2019 meeting is the template.
Odds: 1.72
Three of the last four H2H meetings cleared the 2.5-goal line, Chertsey's attack is among the most productive at Step 3, and Sheppey's recent improvement has come with an uptick in goals at both ends. Our over/under betting guide flags this price as generous for a fixture with such a consistent goals profile.
Odds: 1.75
The Ites have scored in the majority of their home fixtures this season and will fancy set-piece opportunities against a Chertsey defence that can be exposed by direct, physical forward play. Meanwhile, Chertsey have too many scorers to envisage a blank. If you want insurance against the draw, pairing this with double chance cover on Chertsey is a conservative alternative.
Odds: 13.00
Our model's most likely exact outcome. Chertsey's attacking depth suggests a multi-goal away win, but Sheppey's set-piece threat and home cup pedigree make a home goal highly probable. High-risk, high-reward - consult our correct score tips page before staking, and keep speculative plays small.
π Final Score Prediction
Match Analysis
We expect Chertsey to control the tempo for long spells, stretching Sheppey through Bowerman's width and Mazzone's channel runs. The Ites will compete ferociously and should create chances from Leonard's delivery and Bradshaw's aerial presence - enough to get on the scoresheet - but the visitors' extra class in the final third and superior bench depth point to a 3-1 away victory. Sheppey's best hope is an early goal to ignite the Holm Park crowd; if Chertsey score first, the tie could open up quickly. For a safer angle on the same view, Chertsey on draw no bet at around 1.36 removes the replay risk entirely.
The second half is where we see the game decided. Sheppey's intensity tends to dip after the hour mark, and Chertsey's habit of finishing strong - combined with the seven-substitute cup rule giving Little fresh legs off the bench - supports a late flourish. A 1-1 scoreline at half-time shifting to 1-3 by full-time is our most probable script. Chertsey feature prominently in this weekend's banker of the day column, and the 1-3 correct score is the speculative value play for those chasing bigger returns.
Key Insights & Statistics
- Chertsey Town are unbeaten in the last three head-to-head meetings, winning the most recent encounter 4-1 in September 2019.
- Three of the four all-time meetings between the clubs have produced Over 2.5 goals and both teams to score.
- The Curfews have collected 10 points from their opening six Southern Premier South matches in 2026/27.
- Sheppey have won back-to-back Isthmian South East fixtures after a slow start, including victory over Peacehaven & Telscombe.
- Jack Mazzone scored 30 goals in all competitions for Chertsey in his breakout 2024/25 season.
- Chertsey have won three of their last six away matches; Sheppey's Holm Park home form has been mixed.
- The winners receive more than Β£5,000 in FA Cup prize money and a place in the fourth qualifying round.
- A draw sends the tie to a replay at Alwyns Lane in midweek - factor that into draw no bet and double chance selections.
- For more English non-league and EFL coverage, see our Salford vs Grimsby prediction and Notts Co vs Chesterfield prediction.
- Track live scores and in-play markets via our livescores page, and build weekend multiples with our acca tips.
Conclusion
This is a classic FA Cup qualifying conundrum: the romance of a home upset against the cold logic of league standings. Sheppey United have the crowd, the cup pedigree, the improving form and the emotional resonance of the Batten family story to make life deeply uncomfortable for the division-above visitors. Chertsey Town have the deeper squad, the proven goalscorer in Jack Mazzone, the creative wildcard in Seb Bowerman, and a head-to-head record that reads like a warning. Cup ties at this level are often decided by fine margins - a set piece, a goalkeeping moment, a slice of Holm Park wind - and that is precisely why neutral observers should not expect a procession.
Ultimately, though, we side with quality and depth. Chertsey's unbeaten run against the Ites, their strong start to the Southern Premier South campaign and their multi-faceted attack give them the clearest route to the fourth qualifying round. Our prediction is a competitive, entertaining contest that finishes Sheppey United 1-3 Chertsey Town, with the visitors pulling away in the final half-hour as the substitutes make their mark. The recommended plays are Chertsey to win at 1.83 as the anchor, supplemented by Over 2.5 goals at 1.72 and both teams to score at 1.75, with the 1-3 correct score at 13.00 reserved for small-stake speculation.
Whatever happens on Saturday afternoon on the Isle of Sheppey, both clubs can take pride in what they represent: 1890-founded institutions still anchoring their communities more than 135 years later. Enjoy the tie, follow every kick via our livescores service, and keep checking today's football predictions for updates as team news is confirmed. And if you are combining this selection with other fixtures, our acca tips page shows how to structure multiples sensibly. Gamble responsibly - 18+.
