Chesterfield vs Portsmouth

, KO: 12:15 Nov 5, 2023, SMH Group Stadium

National League side Chesterfield welcome League One leaders Portsmouth to the SMH Group Stadium for an FA Cup first round clash on Sunday. Both teams have made fine starts to their respective league campaigns but Pompey will be confident of claiming the upper hand given their superior quality.

Chesterfield have looked imperious this season as they have suffered just one defeat across all competitions so far. Paul Cook’s men are currently on a five match winning run and are two points clear at the top of the National League standings.

The Spireites head into Sunday’s FA Cup first round off the back of a 3-1 National League victory at Kidderminster Harriers. Oliver Banks netted a brace while Will Grigg added the third deep unto added time.

Driven by the impressive Will Grigg, Chesterfield have been prolific in attack, scoring at least two goals in each of their last seven home matches. They have also kept clean sheets in their last three matches at SMH Group Stadium, although those results have been against fellow National League sides.

Playing two tiers above Chesterfield, Portsmouth are also looking impressive in League One at the moment. They are three points clear at the top of the League One standings and are unbeaten in their last 11 matches across all competitions, claiming nine wins in that run.

Portsmouth are coming off a 3-2 victory over Reading in their previous League One fixture. They fought back from two goals down with Tino Anjorin and Colby Bishop pulling them level at the break before Terry Devlin netted the winner in the second half.

The result at Reading highlights a solid away record for Portsmouth, who are unbeaten in their last eight matches on the road, claiming five wins in that run. However, John Mousinho’s men are a bit unconvincing at the back, keeping just one clean sheet in the last five matches in that run.

How the bookies view it

Portsmouth have the upper hand among the bookies with a win priced at 19/20 with William Hill. A victory for Chesterfield is valued at 13/5 by Paddy Power while BetVictor is also offering odds of 13/5 for a draw.

Head to head

Both teams met during the 2013-14 League Two season with Chesterfield avoiding defeat in both fixtures. They claimed a 2-0 victory at Fratton Park before holding out for a 0-0 draw at home.

Players to watch

Chesterfield have looked sharp going forward this season with Will Grigg often applying the finishing touch in attack. The striker has four goals in his last three matches and is priced at 11/5 by bet365 to find the net on Sunday.

Portsmouth are also solid going forward with Colby Bishop netting nine times already this season. The forward could be worth keeping an eye on to score anytime on Sunday at 13/10 with bet365.

Anything else catch the eye?

Chesterfield have seen over 3.5 goals in six of their last seven matches and a repeat could be on the cards at 7/4 with Paddy Power. Both teams often take a while to find their rhythm and could be backed to score in the second half at 7/4 with bet365.

With both teams expected to score after the break, the second half could be tipped to produce the most goals at evens with Paddy Power.

This match between Chesterfield and Portsmouth will be played on Nov 5, 2023 and kick off at 12:15. Check below for our tipsters best Chesterfield vs Portsmouth prediction. You may also visit our dedicated betting previews section for the most up to date previews.

Chesterfield Form
28 Oct 23
Kidderminster Harriers
1 - 3

24 Oct 23
4 - 0
York City

14 Oct 23
5 - 0
Kettering Town

7 Oct 23
Boreham Wood
0 - 2

3 Oct 23
2 - 0

Portsmouth Form
28 Oct 23
2 - 3

24 Oct 23
Cambridge United
0 - 0

21 Oct 23
1 - 0
Carlisle United

10 Oct 23
5 - 1

7 Oct 23
2 - 0
Port Vale

Chesterfield vs Portsmouth Betting Tips & Predictions
Portsmouth to win
William Hill
Colby Bishop anytime goalscorer
Over 3.5 goals

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