While the home side are challenging for promotion in the Championship, National League South side Maidstone are attempting to create further history after their miraculous win at Ipswich Town in the previous round.
Match preview
Having suffered just one home defeat in 16 Championship matches during 2023-24, Mark Robins would have expected to see his Coventry side earn at least a share of the spoils against Preston North End on Friday night.
Instead, the visitors produced one of their best performances of the season to run out 3-0 victors, moving above Coventry in the table and into seventh position.
After losing just twice in their previous 21 fixtures in all competitions, it is a wake-up call for the Sky Blues who had the chance to move into the playoff spots ahead of the remainder of the weekend fixtures.
Although this competition could be perceived to be a distraction, Robins will now welcome it in a bid for his players to rediscover some form and move closer to an appearance at Wembley Stadium.
Coventry have defeated Oxford United and Sheffield Wednesday, courtesy of a replay, to progress through to the last 16 of the competition.
In sharp contrast, Maidstone have come through seven ties - without the need of a replay - in what is proving to be one of the most famous runs in FA Cup history.
The sixth-tier side played each of the fourth qualifying rounds away from home before recording victories over EFL opposition in Barrow and Stevenage at the Gallagher Stadium.
However, their crowning moment - so far - came at Portman Road as they remarkably posted a 2-1 win over Championship side Ipswich Town, scoring with their only two shots and withstanding all but one of 38 efforts from their hosts.
Not since 1978 has a team from below the fifth tier reached the fifth round of the FA Cup, and it comes at a time when they are trying to earn a return to the National League.
George Elokobi's side have recently dropped down to sixth position in the National League South, warming up for this fixture with a 1-1 draw at home to Hemel Hempstead Town and 2-0 defeat at Aveley.
Coventry City FA Cup form:
W
D
W
Coventry City form (all competitions):
L
W
W
D
W
L
Maidstone United FA Cup form:
Maidstone United form (all competitions):
Team News
Robins will inevitably make changes to his Coventry XI with Jake Bidwell, Liam Kelly, Victor Torp, Kasey Palmer and Matt Godden all in line for recalls.
Liam Kitching should be restored to the centre of the defence, while goalkeeper Brad Collins may potentially return between the sticks having not featured since February 14.
Tatsuhiro Sakamoto is unavailable after suffering what appeared to be a serious injury in the first half versus Preston, joining Ben Sheaf and Jamie Allen on the sidelines.
Of the players that started the Ipswich game, Harry Kyprianou was the only player absent from the Maidstone team that began the Aveley game.
Should he not feature, Reece Greenidge should deputise in defence, but much may depend on whether Elokobi chooses to change formation for another fixture of this magnitude.
Coventry City possible starting lineup:
Collins; Van Ewijk, Thomas, Kitching, Bidwell; Kelly, Torp; Tavares, Palmer, Wright; Simms
Maidstone United possible starting lineup:
Lucas; Hoyte, Fowler, Appiah, Greenidge; Corne, Bone, Berkeley-Agyepong; Sole, Duku, Reynolds
We say: Coventry City 3-0 Maidstone United
With Coventry suffering a surprise defeat at the hands of Preston, and in convincing fashion too, Maidstone will sense an opportunity to take advantage. However, Robins may now select a stronger Coventry starting lineup than previously planned, a factor which may prove decisive.