This Week's Opposition: Chesterfield

Photo Credit: Chesterfield FC

After going 2-0 down at the Select Car Leasing Stadium last Saturday, the Blues came back with 3 goals in reply to Reading, bringing home 3 points and remaining unbeaten at the top of League One. Next up for Pompey, a break from league matters.

John Mousinho will next lead his side into FA Cup action.

Their opponents for this weekend’s First Round clash on the road is non-league outfit Chesterfield, who have a few familiar faces plying their trade with the club.


Former Pompey boss Paul Cook is currently at the helm for the Spireites.

Cook once worked as a central midfielder during a playing career that spanned 23 years, before moving into management in 2006 with Southport.

He also managed Irish side Sligo Rovers and Accrington Stanley. Cook has also taken charge of Chesterfield once before prior to this current stint with the club - He was able to guide them to the League Two title in the 2013/14 season, which was also the last time these 2 sides met.

In May 2015, the 56-year-old was appointed as manager of Portsmouth with the club then in League Two. After a failed Play-Off campaign at the end of his first season in charge, Cook went on to lead the Blues to promotion to the 3rd tier in April 2017, before then winning the League Two title on the final day of the season with an emphatic 6-1 victory over Cheltenham Town at Fratton Park.

That would be Cook’s final act as Pompey manager - He left shortly after the promotion party and went on to take charge of Wigan Athletic, guiding the club to an instant return to the Championship in his first his year in charge.

Cook resigned as Wigan manager in July 2020 after the club fell into administration and were relegated back down to League One following a hefty points deduction - They had been on course to finish around mid-table without the points taken away.

After a short stint at Ipswich Town, Cook returned to Chesterfield in February 2022 for his second spell in charge - Former Portsmouth midfielder Gary Roberts is currently serving as his assistant.


Our one to watch is another familiar face, Michael Jacobs.

The attacking midfielder began his career at Northampton Town and made his professional debut in 2009. He then went on to win back-to-back Player of the Season awards in 2011 and 2012.

Jacobs moved to Championship side Derby County in 2012, before going out on loan to Wolverhampton Wanderers, who he would sign for on a permanent deal the following season in 2014.

The now 31-year-old then moved on to Wigan Athletic and ended up spending 5 years at the DW Stadium before signing for Pompey in September 2020, when Kenny Jackett was manager of the club.

Jacobs would amass 76 competitive appearances during his 3-year spell with the Blues, after which he signed on a free for Chesterfield, following the expiration of his contract at Fratton Park back in the summer.

It’s important to note that another former Blues midfielder, Tom Naylor, is also playing for Chesterfield!


With 8 league goals to his name at this stage of the season, former Wigan and Sunderland striker Will Grigg is currently Chesterfield’s leading scorer.WillGrigg_Chesterfield

Grigg, who signed for The Spireites for an undisclosed fee on a 3-year deal from MK Dons back in June, has scored 3 goals in his last 2 appearances for the club, bagging a brace against York City before netting in last week’s victory away at Kidderminster Harriers.

Prior to those strikes, the 32-year-old had gone 5 games without scoring.

Between 2012 - 2018, Grigg had represented the Northern Ireland senior team 13 times, scoring twice.

Those of a Pompey persuasion will be hoping Will Grigg is not on fire this weekend.


Whilst Pompey go into this tie with the confidence of a 26 game unbeaten streak in the league, their opponents Chesterfield will also have a similar vein of momentum behind them.

Paul Cook’s side are undefeated in their last 12 league outings, 13 in all competitions if you include their 5-0 thrashing of Kettering in the final round of Qualifying for The FA Cup.

The Spireites sit pretty at the top of the National League with 44 points on the board from 17 matches played and have only lost 1 league fixture all season. They have a 2 point cushion over 2nd-placed Barnet, having also played a game fewer.

The last time these 2 sides met was back on the 3rd of March, 2014 when the clubs were playing in League Two - That game ended in a goalless stalemate on Chesterfield’s home turf with Paul Cook in the dugout for the hosts and Richie Barker managing the opposing bench for the Blues.

Who will progress to Round 2 of this year’s FA Cup? Can Pompey get the better of some familiar faces?

Tune in for all of the unmissable action of Portsmouth's FA Cup First Round clash with Chesterfield when Pompey Live returns this Sunday (November 5th) from 11am!

Kick-off: 12:15pm


Add a comment

Log in to the club or enter your details below.
Weather in Portsmouth
Monday Sunny intervals High 18°C   Low 12°C
Tuesday Medium-level cloud High 20°C   Low 12°C

Coming Up

  • Express Breakfast with Ian James

    6:30am - 10:00am

    Start your day the Portsmouth way with great music, fun and games alongside local guests from all walks of life and the latest travel news to guide you through rush hour in the city. Represented by Biscoes Solicitors.

  • Paul Marsh

    10:00am - 1:00pm

    The Pompey man with the mid-morning plan brings you great music, interviews and shares everything you need to know about what's going on in the great waterfront city. Hand-crafted by Coffee Cup.

Recently Played


Listen to Express FM