The National League side held their higher-tier opponents to a 1-1 draw in the first meeting last month and ought to travel to the Priestfield Stadium optimistic of recording a cup upset.
Match preview
League Two strugglers Gillingham needed a replay to get the better of National League North side Fylde in the first round of the FA Cup, and that 1-0 success marks just one of two wins for Neil Harris's men in their last 12 games, the other being a memorable penalty-shootout EFL Cup win over Brentford.
However, progression in the cup competitions has not offered much of a silver lining for the Gills amid their dismal fortunes in the fourth tier, with their most recent match ending in a comprehensive 3-0 defeat to Salford City on Saturday courtesy of strikes from Theo Vassell, Ryan Watson and Callum Hendry.
While Harris accepted most of the blame for that loss, he pulled no punches when criticizing his players' failures to put the ball in the back of the net, and Gillingham are now without a win in League Two since beating Sutton United 1-0 on October 1.
Harris's men have now failed to score in each of their last six League Two matches during an abysmal run of profligacy, and they have only amassed a measly six league goals all season long - unsurprisingly the worst tally in the division by far as they sit 23rd in the table.
If Harris was not already on borrowed time, an early FA Cup exit to lower-league opposition could very well accelerate any decision from the powers-that-be, but their opponents also come into Thursday's game on the back of a disappointing defeat.
Dagenham & Redbridge were seconds away from dumping Gillingham out of the FA Cup in their second-round meeting following Josh Walker's 80th-minute opener, but Harris's men forced a replay through Scott Kashket's injury-time leveller at Victoria Road.
Prior to holding the League Two strugglers to a score draw, Daryl McMahon's men had put seven past Beckenham Town and claimed a 1-0 win over Maidenhead United to advance to the second round, and they reached the third round as recently as the 2015-16 season before being eliminated by Everton.
The Daggers are outsiders when it comes to pushing for a playoff place in the National League - sitting 10th in the table with eight wins, five draws and seven defeats from their first 20 matches, but a three-game winning streak in the fifth tier was brought to an end last time out.
McMahon had led his side to successive wins over Wealdstone, Solihull Moors and Scunthorpe United before Will Goodwin scored the only goal of the game in a 1-0 success for Torquay United at the weekend, but their proposed meeting with Gateshead this weekend has been postponed due to their FA Cup commitments.
There is more than one motivation for Harris and McMahon to conjure up a winning performance here, as whichever team comes up trumps in Thursday's game will have the honour of hosting 2020-21 winners Leicester City in the third round.
Gillingham FA Cup form:
D
W
D
Gillingham form (all competitions):
L
W
L
D
D
L
Dagenham & Redbridge FA Cup form:
Dagenham & Redbridge form (all competitions):
W
W
W
W
D
L
Team News
Gillingham defender Dave Tutonda is stepping up his recovery following a knee operation two months ago and is now back in training with the squad, but the weekend's clash with Salford came too soon for him to make a comeback.
Olly Lee is also an uncertainty as he rehabilitates following a broken toe, while striker Callum Harriott is not quite ready for first-team action either, with Harris admitting that the ex-Reading man would need "a few weeks" to get up to speed.
Midfielder Robbie McKenzie and defender Elkan Baggott will also need assessing after picking up groin and head injuries at the weekend, so Haji Mnoga could be brought back in amid reports of Portsmouth preparing to recall the Tanzania international in January.
As for Dagenham, goals have not been an issue for McMahon in recent times, as strike partners Junior Morias and Walker have 14 between them this term and ought to start up front.
The visiting manager should keep faith with the majority of the XI from last week's 1-1 draw, although Joel Taylor was brought back into the side in place of Mo Sagaf and could hold his place in a 3-5-2 setup.
Gillingham possible starting lineup:
Turner; Alexander, Wright, Ehmer, Mnoga; Jefferies, Williams; Adelakun, Reeves, Kashket; Mandron
Dagenham & Redbridge possible starting lineup:
Justham; Onariase, Haire, Phipps; Weston, Mussa, Robinson, Rance, Taylor; Morias, Walker
We say: Gillingham 0-0 Dagenham & Redbridge (a.e.t, Gillingham win on penalties)
It is extremely difficult to see where the goals are going to come from in this Gillingham side at the moment, and we would not be at all surprised to see this one go the distance as a resilient Dagenham hold out for another draw.