At a time when the home side sit bottom of the Premier League table, Gillingham occupy the same position in League Two.
Match preview
Sitting four points adrift of safety in the top flight, Wolves and Julen Lopetegui have plenty to be concerned with going forward, yet Tuesday's encounter with Gillingham feels like the start of a new era.
If reports are to be believed, the Spaniard intends to go on a signing spree in January with some high-profile names in line to arrive at Molineux, seemingly ripping up the process of buying younger players with potential to sell for a profit in later years.
Wolves have an important and testing restart in equal measure. After this game, fixtures with Everton, Manchester United and Aston Villa loom before a trip to Liverpool in the FA Cup.
However, for now, at least, Lopetegui will be focused on trying to move Wolves through to their first EFL Cup quarter-final for 27 years.
In the build-up to this match, Wolves have played Empoli and Cadiz in friendlies, drawing with the Italian side before coming through a thriller with the La Liga outfit by a 4-3 scoreline.
From Neil Harris's perspective, this encounter features down the list of the club's priorities at a time when they are battling to remain in the EFL.
Gillingham currently sit in last place in the fourth tier, albeit with a match in hand on some of the teams above them and being just a point adrift of 21st spot.
However, this squad are well refreshed after a couple of postponements, and they will view this as an opportunity to potentially set up a money-spinning last-eight tie.
Gillingham are already in that position having been drawn at home to Leicester City in the FA Cup third round, something which arguably takes the pressure off this contest given that they know extra income is already coming through the door.
The Kent-based side also showed in the last round that they are capable of overcoming Premier League opposition on away territory, coming from behind to eventually defeat Brentford in a penalty shootout.
Wolverhampton Wanderers EFL Cup form:
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Wolverhampton Wanderers form (all competitions):
Gillingham EFL Cup form:
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Gillingham form (all competitions):
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Team News
During the World Cup break, Lopetegui has experimented with a back three and back four, the latter likely to be used for this contest.
First-choice goalkeeper Jose Sa could get the nod over Matija Sarkic between the sticks having failed to earn any game time with Portugal at the World Cup.
However, Ruben Neves and Matheus Nunes may start among the replacements, giving opportunities to Boubacar Traore and Joe Hodge, while Diego Costa should get the nod over Raul Jimenez down the middle of the attack.
After a 12-day gap, Harris may be willing to start with the Gillingham XI which begun the 3-2 victory over Dagenham & Redbridge in the FA Cup.
Nevertheless, after each of Alex MacDonald and Scott Kashket came off the substitutes' bench to provide an assist in that contest, both players are pushing for chances in the final third.
Wolverhampton Wanderers possible starting lineup:
Sa; Semedo, Collins, Kilman, Bueno; B.Traore, Moutinho, Hodge; Traore, Costa, Podence
Gillingham possible starting lineup:
Turner; Wright, Ehmer, Baggott, Tutonda; Williams, Jefferies; Kashket, Adelakun, Reeves; Walker
We say: Wolverhampton Wanderers 2-1 Gillingham
Despite the gulf in class between these two teams, do not necessarily expect a one-sided contest. However, while Wolves may require some time to get up to speed under Lopetegui, we still expect the hosts to edge this contest by a narrow scoreline.