Entering arguably their biggest match of the season, Portmore United will do so against leaders Harbour View under a new coach Linval Dixon, who replaces Andre Waugh.
Portmore United, in second spot on 47 points, have a 12-point deficit to make up on Harbour View, who are sitting pretty on 59 points. This change of personnel at the helm might just be the tonic they need, or it could prove to be very toxic.
Dixon, who held the head coach position at Portmore United in 2007 and again in 2010, has just taken Old Harbour Bay United to the semi-final of the LIME St Catherine Major League.
He could not be reached for a comment yesterday, but the Jamaica Observer was informed that training went well yesterday morning.
Just how the Portmore players will respond is left to be seen. But today's encounter against Harbour View could mean the end of their season if they lose, as that would give Harbour View a 15-point lead with only nine games remaining.
The 'Stars of East' head coach Vin Blaine is not sure how the Portmore players will respond to the change of coach, but he is not taking anything for granted.
"A win would be 15 points ahead of Portmore and I think that would practically almost seal the title. It is a very important game for us. We want to win that game definitely," said Blaine.
"It might affect their approach. I don't know mentally where they are now, it could be positive, maybe the players didn't want the coach and if a new coach comes in they might be comfortable. I really don't know the background issue why he left or why he was moved out of the position, I am only interested in going and playing our football. They have to worry. They can't lose. We are under no pressure. They are under pressure," noted Blaine.
At the other end of the spectrum, there will be two crucial relegation battles on with bottom-placed Savannah FC on 18 points travelling to Brancourt to play ninth-placed Sporting Central Academy on 33 points.
Westmoreland-based Savannah are 15 points away from safety and a defeat today against one of the teams they are hoping to catch could spell disaster.
The same scenario for 11th-placed Highgate United, on 25 points, when they host 10th-placed Humble Lion, on 33 points, at Drax Hall. With an eight-point deficit to make up, Highgate cannot afford to lose with just nine games remaining after today's encounters.
Meanwhile, third-placed Boys' Town, on 45 points, take on seventh-placed Tivoli Gardens, on 36 points, in what is expected to be an exciting match at Collie Smith Drive.
The 'Red Brigade' still harbour thoughts of winning the title, although being 14 points adrift, and will want to complete the hat-trick of wins and bragging rights over their fierce rivals for the season.
There will be a double header at Drewsland on Monday night with eighth-placed Cavalier, on 36 points, playing sixth-placed Montego Bay United, on 40 points, in a battle for a top-six spot, starting at 5:30 pm.
In the feature encounter at 9:15 pm, fourth-placed Waterhouse, on 44 points, tackle fifth-placed Arnett Gardens, two points below them in what is expected to be an exciting shoot-out between the two teams with the two leading goalscorers in Jermaine Anderson, with 16 strikes, and Kirk Ramsey, with 12 goals.
3:30 pm Boys' Town vs Tivoli Gardens @ Collie Smith Drive
3:30 pm Highgate United vs Humble Lion @ Drax Hall Sports Complex
3:30 pm Sporting Central Academy vs Savannah @ Brancourt
7:00 pm Portmore United vs Harbour View @ Ferdie Neita Park