Both sides are competing at opposite ends of the table, with the hosts just a spot above the relegation zone while the visitors are only three points off the last playoff spot.
Match preview
Colchester's recent form paints a grim picture, having seven losses in their last eight League Two matches, including a 5-3 defeat to AFC Wimbledon last time out, which has left them just six points above the drop zone.
Cameron McGeehan, Joe Taylor and Tom Dallison found the net, but it was not enough to stop Matt Etherington's side from losing a second league match in a row.
Scoring three goals against Wimbledon offers a glimmer of hope, but conceding 58 shots and six goals in two games raises defensive concerns that manager Etherington needs to tighten the backline.
Colchester can find solace in the fact that their last league win was on home turf and they have beaten Gillingham twice in their last three meetings.
However, their last home win against the Gills dates back to 2015 in League One, a run they will be eager to halt on Monday.
Meanwhile, Gillingham snapped their winless streak with a narrow 1-0 victory over Sutton United on Friday, courtesy of Scott Malone's late strike.
Like most of their recent fixtures, Stephen Clemence's men were on the front foot, creating several chances and managing to convert one in the end.
The result saw the Gills climb to 10th place in the League Two table and are only three points adrift of the last playoff place heading into the new year.
However, Clemence's men will have to find a way to end their current three-match winless streak on the road to boost their chances of finishing in the playoff zone.
With four consecutive away wins against Colchester in all competitions, the Gills will be optimistic about their chances of getting a favorable result on Monday.
Colchester United League Two form:
L
L
L
W
L
L
Colchester United form (all competitions):
L
L
L
W
L
L
Gillingham League Two form:
L
W
L
D
L
W
Gillingham form (all competitions):
W
W
L
D
L
W
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Team News
The hosts will be without McGeehan, who is suspended after picking up a red card against Wimbledon last time out, and he will likely be replaced by Al-Amin Kazeem in the starting lineup.
The U's will also be without Fiacre Kelleher, Nico Lawrence and Jay Mingi due to muscular problems.
Clemence is likely to stick to the same side that got maximum points against Sutton United.
Oliver Hawkins will continue to pair Ashley Nadesan in attack, while Jonathan Williams will play the supporting role.
Colchester United possible starting lineup:
Goodman; Egbo, Mitchell, Hall, Iandolo; Chilvers, Read; Fevrier, Kazeem, Jay; Taylor
Gillingham possible starting lineup:
Turner; Masterson, Ehmer, Ogie; Clark, Coleman, Jefferies, Alexander; Williams; Nadesan, Hawkins
We say: Colchester United 1-2 Gillingham
This match promises to be a tight and tense affair, with both sides desperate to get their 2024 off to a bright start.