Hornets will be just too strong for Village
Young Men's Social Club v
X'Roads
A closely contested match at Bernard Park between two evenly matched sides could well come down to each team's top goalscorer.
In Ricky Saltus, X'Roads have one of the deadliest finishers in the First Division in their ranks, while Social Club also have an equally dealy finisher in Clay Darrell.
Whichever striker puts away his chances will probably decide this one.
Prediction: X'Roads 3-1
PHC v MR Onions
At first glance this match appears completely one-sided, and it could get out of hand given MR Onions have half their side leaving the Island for the holidays, or out through injuries.
However PHC will not take Onions lightly given that this will be their last match before the break, and they will want to end the first half of the season on a winning note at Southampton Oval.
All should be plain sailing for the Premier Division club, as long as 'keeper Raymond Glasford improves upon his recent performances for Zebras.
Prediction: PHC 4-0
Devonshire Cougars v
BAA
The biggest mismatch of the round, the question will not be who scores, but rather how many the home side knock in at Devonshire Rec.
But, given the poor finishing in their last league match over the weekend against Parish, Cougars could quite easily make life difficult for themselves in a competition which has a habit of bringing the top teams down a peg or two.
Realistically though this should be nothing more than a training run for Cougars, who will be happy for a run out ahead of their altogether tougher friendly against Trinidad on December 30.
Prediction: Cougars 5-0
North Village v
Dandy Town
The match of the round will pit the Premier Division's in-form teams against each other at Bernard Park.
In their last meeting, both missed chances to take three points in a tame draw.
The result should be different this time around with Hornets finally showing their championship pedigree, while the Rams will be looking to rebound from their weekend loss to Somerset Eagles.
Home field advantage may play a part, but whoever gets the first goal will end up winning this one.
Prediction: Town 2-3
Southampton Rangers
v Robin Hood
This will be the most fascinating match of the weekend as the First Division leaders look to claim a Premier Division scalp at Southampton Oval.
With Rangers' defence shipping goals in recent matches, anything can be expected although their performances as of late have been without key players.
They will need to be more productive with the ball in order to get to the next round.
In Robin Hood, they will line up against a well organised side that have the ability to break them down, and have conceded just one goal in the league all season.
Prediction: Rangers 3-1
Hamilton Parish v
St. David's
High-flying St. David's will try their best to not get dumped out in the first round for the second successive year at Wellington Oval.
This time around they face off against a Parish side looking to end the first half of their campaign with a spot in the second round.
Having fought hard for their draw against Cougars, they can't afford to let their foot off the gas with the likes of Sean Boddington and Dejuan Paynter lying in wait.
With Nigel Burgess in goal and Jamie Smith up front, they may have the edge in this one.
Prediction: Parish 3-2
Boulevard v Wolves
The cup holders should advance with a win, but they may not have it all their own way if they take Wolves lightly at St. John's Field.
Getting a win under their belt last week was essential to get Blazers' league campaign back on track, and now a win in a competition they are looking to defend willl give them added confidence.
But Wolves possess the weapons to trouble them if they aren't careful. With Vincent Minors Jr. and Derrick Brangman, they have the attack, but Wolves' back four must remain tight if they are to have any chance in this match.
Prediction: Blazers 4-1