The Spireites are well on course for promotion to the Football League following a sensational start to the campaign, whilst recently-promoted Orient are still finding their feet in the third tier.
Match preview
Chesterfield extended their winning run at SMH Group Stadium across all competitions to a remarkable 10 matches last Saturday after earning three points from a five-goal thriller against Eastleigh in the National League, with Paul Cook's men recording their 17th success of the league campaign.
The Spireites raced into a three-goal lead in the opening 25 minutes of the second period thanks to a brace from Oliver Banks and a strike by former Wigan Athletic forward Will Grigg, and although the visitors managed to pull two goals back via Scott Quigley and the division's leading goalscorer Paul McCallum, the hosts were able to hold on for the victory.
As highlighted by Chesterfield on their social media channels as they attempt to sell out their Derbyshire home this weekend, Cook's charges are the highest scorers in the English game so far in 2023-24, making the net ripple on an outstanding 53 occasions in just 21 fifth-tier matches.
On top of terrorising non-league backlines in the early stages of the term, the Spireites also caused the current League One pacesetters huge problems in the first round of the FA Cup last month, with Tom Naylor's first-half goal dumping John Mousinho's Portsmouth out of the competition.
After netting seven goals in 16 league appearances at the beginning of the campaign, attacker Joe Quigley has recently been rewarded with a contract extension at Chesterfield, committing his future to the National League leaders until the summer of 2025, and the 26-year-old is almost a certain starter on Sunday.
Leyton Orient will travel to Derbyshire on Sunday afternoon in the midst of a five-game winless streak across League One and EFL Trophy action, however the League Two champions have managed to halt a three-game losing streak with successive 1-1 draws against Wigan and most recently Bristol Rovers.
Midfielder Grant Ward netted his first of the league campaign for the Gasmen on Tuesday to put them ahead just before the half-time interval at the Memorial Stadium, and it looked as if the O's would have to settle for a fourth loss in five matches until Tristan Crama bundled the ball into his own net in the 93rd minute.
Following an eight-season absence from the third tier of English football - which included a two-year stint in the National League - Orient's steady tally of 22 points from 19 matches has given them a foothold on their return to League One, with 21st-placed Fleetwood Town currently six points behind.
Richie Wellens's side secured their place in the second round of the FA Cup after a 3-1 win over Carlisle United last month, with Joe Pigott, Aaron Drinan and Cypriot Ruel Sotiriou all getting onto the scoresheet during the O's only victory in their last nine matches in all competitions.
Sunday's visitors were winners by an identical scoreline when they last faced Chesterfield when both sides plied their trade in non league back in the 2018-19 season, and the promotion-chasing Spireites have only managed a single victory against the O's in their previous six meetings.
Chesterfield FA Cup form:
Chesterfield form (all competitions):
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Leyton Orient FA Cup form:
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Leyton Orient form (all competitions):
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Team News
Chesterfield have confirmed that they will be without the services of defender Tyrone Williams this weekend due to injury, although the 29-year-old has returned to training on the grass this week.
Midfielder Mike Jones will be unavailable for selection after picking up his 10th yellow card of the season in the loss at Southend United, meaning the former Sheffield Wednesday man has to serve a two-match suspension.
Albanian Armando Dobra was a real handful for Portsmouth last month and Championship side West Bromwich Albion during last season's FA Cup, and the 22-year-old will fancy his chances of making an attacking impact on Sunday afternoon.
Leyton Orient are expected to be missing the presence of winger Jordan Graham once again this weekend, with the ex-Birmingham City player leading his side's assist charts despite not featuring since late October.
Wellens is likely to make a couple of alterations to the side which drew at Bristol Rovers in the week, with the likes of Pigott and Daniel Agyei pushing for starts in offensive areas.
Shaqai Forde could have bagged his fourth goal of the season at the Memorial Stadium but was let down by some poor touches, although the 19-year-old should be handed the opportunity to redeem himself this weekend.
Chesterfield possible starting lineup:
Tyrer; Mandeville, Palmer, Grimes, Horton; Naylor, Oldaker, Jacobs, Banks, Quigley; Grigg
Leyton Orient possible starting lineup:
Brynn; Hunt, Turns, Happe, Sweeney; Brown, Mizouni, Sanders, Sotiriou, Archibald; Forde
We say: Chesterfield 2-1 Leyton Orient
Chesterfield have proven themselves to be levels above the chasing pack in the National League this term, and the Spireites will have no fear as League One opposition arrives in town this weekend.