Sheppey United vs Chertsey Town Prediction & Betting Tips

Last updated 27 Sep 2026
Sheppey United
Sheppey United
England FA Cup
03.10.2026    15:00
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Chertsey Town
Chertsey Town

Sheppey United host Chertsey Town in the FA Cup. Chertsey have been winning regularly of late, while Sheppey have found results much harder to come by.

The two clubs rarely meet, so there's not much history to lean on here. What we do have is a clear form gap heading into this one, and that's where the analysis starts.

Analysis updated .

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Form: Chertsey flying, Sheppey struggling

Chertsey Town's last 20 matches make for decent reading: 11 wins, 5 draws and just 4 defeats, with 42 goals scored against 29 conceded. That sample covers league games, FA Cup ties and a handful of friendlies, so it's not a clean league record, but the direction of travel is clearly positive.

Sheppey United: 20 completed matches; Chertsey Town: 20 completed matches.

Sheppey United

20 matches
Win
15% 3 / 20
Draw
20% 4 / 20
Loss
65% 13 / 20
Scored
18
Conceded
46
Difference
-28

Chertsey Town

20 matches
Win
60% 12 / 20
Draw
25% 5 / 20
Loss
15% 3 / 20
Scored
45
Conceded
30
Difference
+15
Sheppey United
League Home Away Date Score
FA Cup Snodland Sheppey United 19.09.2026 0-1
FA Trophy Deal Town Sheppey United 12.09.2026 3-0
FA Cup Redhill Sheppey United 05.09.2026 1-2
FA Trophy Beaconsfield Town Sheppey United 29.08.2026 1-1
Non League Div One - Isthmian South East AFC Croydon Athletic Sheppey United 25.04.2026 2-2
Non League Div One - Isthmian South East Sheppey United Crowborough Athletic 18.04.2026 1-2
Non League Div One - Isthmian South East Sheppey United Sevenoaks Town 11.04.2026 1-6
Non League Div One - Isthmian South East Faversham Town Sheppey United 06.04.2026 3-0
Non League Div One - Isthmian South East Sheppey United Three Bridges 04.04.2026 1-2
Non League Div One - Isthmian South East Eastbourne Town Sheppey United 28.03.2026 3-1
Load more
Chertsey Town
League Home Away Date Score
FA Trophy Welling United Chertsey Town 26.09.2026 2-3
Non League Premier - Southern South Chichester City Chertsey Town 22.09.2026 2-2
FA Cup Chertsey Town Greenwich Borough 19.09.2026 3-2
Non League Premier - Southern South Chertsey Town Malvern Town 12.09.2026 5-0
FA Cup Carshalton Athletic Chertsey Town 07.09.2026 1-2
FA Cup Chertsey Town Carshalton Athletic 05.09.2026 1-1
Non League Premier - Southern South Hanworth Villa Chertsey Town 31.08.2026 4-1
Non League Premier - Southern South Chertsey Town Frome Town 29.08.2026 1-2
Non League Premier - Southern South Sholing Chertsey Town 22.08.2026 2-4
Non League Premier - Southern South Chertsey Town Yate Town 15.08.2026 1-1
Load more

Sheppey United's equivalent stretch tells a different story. Three wins from 20, 13 defeats, and a goal difference of 18 for against 46 against. They've conceded freely across FA Cup, FA Trophy and league fixtures stretching back to January, and the goals-against tally in particular stands out.

Chertsey arrive with real momentum; Sheppey's defensive numbers are the bigger concern.

Comparative Team Statistics: Sheppey United vs Chertsey Town

Sheppey United vs Chertsey Town statistics: team strength, attack, defence and head-to-head comparison.

One previous meeting, back in 2019

These two have only met once on record, an FA Cup tie in September 2019 that Chertsey Town won 4-1, hosted at their own ground rather than Sheppey's. That's seven years ago now, with a different venue and almost certainly different squads on both sides, so it doesn't tell us much about how this version of the fixture plays out.

Head 2 Head
League Home Away Date Score
FA Cup Chertsey Town Sheppey United 07.09.2019 4-1
Sheppey United vs Chertsey Town: England FA Cup match preview with team badges and kick-off details.

How this one could go

The clearest thread running through the evidence is the contrast in recent output. Chertsey have been scoring freely and picking up wins across various competitions, while Sheppey have shipped goals at a high rate and won only occasionally. On paper that points towards an away side full of confidence facing a home team short of the same.

FA Cup football at this level can still throw up surprises, though, and cup form doesn't always mirror bread-and-butter league form. Sheppey's numbers include some FA Cup and FA Trophy results mixed in with league games, so there's a bit of everything in that sample rather than a single tidy narrative.

Squad lists and player details

Squad and player details

Sheppey United
Name Country Age Position Height Weight
M. Morris England 25 Midfielder n/a n/a
R.Hamill England 32 Midfielder n/a n/a
J. Bessey-Saldanha England 30 Midfielder n/a n/a
F. Morgan England 24 Defender n/a n/a
Alexander Willis England 27 Attacker n/a n/a
J. Marsh England 21 Attacker n/a n/a
O. Durowoju England 20 Attacker n/a n/a
J. Wisson England 28 Midfielder n/a n/a
D. Bradshaw England 35 Attacker n/a n/a
C. Wilkins England 27 Midfielder n/a n/a
K. Monahan England 20 Midfielder n/a n/a
Danny Leonard England 29 Midfielder n/a n/a
D. Spencer England 25 Midfielder 173 cm n/a
J. Lambert England 25 Midfielder n/a n/a
O. Housego England 28 Midfielder n/a n/a
A. Clark England 20 Midfielder n/a n/a
B. Catherick England 21 Midfielder n/a n/a
J. Bedzrah England 21 Midfielder n/a n/a
C. Nichol England 20 Defender n/a n/a
Briggs Ojemen England 26 Defender n/a n/a
Chertsey Town
Name Country Age Position Height Weight
B. Taylor England n/a Attacker n/a n/a
L. Jackson England n/a Attacker n/a n/a
J. Baxter England n/a Attacker n/a n/a
S. Murphy England 36 Midfielder n/a n/a
C. MacLaren England 39 Midfielder n/a n/a
S. Hurrell England 38 Midfielder n/a n/a
T. Halsey England n/a Midfielder n/a n/a
E. Etukudo England n/a Midfielder n/a n/a
M. Gogonas Greece 29 Midfielder n/a n/a
A. Crossley England 33 Midfielder n/a n/a
M. Abisogun England n/a Midfielder n/a n/a
Q. Rowe England 37 Defender n/a n/a
J. Gasson England 41 Defender 182 cm 71 kg
S. Day England n/a Defender n/a n/a
L. Gallifent England n/a Goalkeeper n/a n/a
S. Ompreon England 25 Attacker 176 cm n/a
O. McCoy England 28 Attacker n/a n/a
J. Mazzone England 33 Attacker n/a n/a
C. Lynch England n/a Attacker n/a n/a
L. Flatman England n/a Attacker n/a n/a

Put simply, Chertsey Town look the sharper side going into this by some distance, but we don't have a market to test that view against, and the evidence we do have is a mixed bag of competitions rather than a clean like-for-like comparison.

Without pricing to weigh up, we're passing on this one rather than guessing at value that isn't there to see.

Who will win?


Sheppey United (0%)
Draw (0%)
Chertsey Town (0%)
Last updated: September 2026
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