The Jamaicans will be looking to secure their second straight victory, when they welcome traditional powerhouses Barbados into the tournament at Sabina Park.
The Guyanese are also eyeing their second consecutive victory, when they face Windward Islands at Windsor Park.
In the other match, Combined Campuses & Colleges and Leeward Islands, two sides that suffered heavy defeats in the first round, will battle for supremacy at 3Ws Oval.
In Kingston, Jamaica, the home team are coming off an 81-run victory over the Windwards and will be looking to follow up against the Barbadians.
The visitors will be playing their first match in the tournament and may be a little rusty, particularly with a couple new faces giving them a boost.
Omar Phillips, the former CCC captain, is expected to make his Barbados debut and open the batting with West Indies opener Kraigg Brathwaite.
Fast-bowling allrounder Chris Jordan, who has played all of his first-class matches for Surrey in the English County Championship, is also likely to make the final cut and give enhance the Barbadian attack and lower-order batting.
Jamaica will be without powerful opener Chris Gayle, whose hundred in the first match put them in an impregnable position, and all-rounder Andre Russell, both off to the Bangladesh Premier League Twenty20.
West Indies batsman Danza Hyatt, dropped for the first game, and left-arm fast bowler Sheldon Cotterrell are two more than capable replacements, who will not compromise Jamaica’s strength.
Neither side has a superior record over the other in recent matches, but the Jamaicans have dominated the matches on home soil, winning four of six.
In Roseau, Dominica, Guyana will feel more comfortable in the conditions and more confident than the real home team Windwards, having conquered the Leewards by a resounding 234 runs in the first round at the same venue.
Windwards, boosted by the return of West Indies captain Darren Sammy, their regular skipper, will be looking to rebound from their defeat against Jamaica and convince the Guyanese that they cannot take over their turf.
Windwards have several reason to take heart that they could send a strong message to their opponents. They have dominated the nine matches played on home turf since the turn of the century, winning three and gaining first innings lead in five of the six drawn matches.
In Cave Hill, Barbados, hosts CCC, who lost by 172 runs in the first round against T&T at the same venue, will be looking to impress new bowling consultant Curtly Ambrose when they face his old side Leewards.
Bowling has been the CCC’s strength, but their batting has blown hot and cold over the years, and they will be looking to improve significantly in this area.
Leewards have dramatically fallen from grace following Ambrose’s exit from the game. They too, have a solid bowling attack, but it is their batting that will also need to come up big to help them maintain their dominance over the CCC.
Leewards have lost only one of the five matches they have contested against the composite side. They have won two of the remaining five and gained first innings lead in the other two.