South Central Confederation champions Rivoli took the lead in the 37th minute through a Luke Soares goal.
But St Mary flag-bearers Highgate, the Eastern Confederation champions, kept their unbeaten run in the play-off series intact, courtesy of goals from Richard Orrett (43rd) and Roen Nelson (75th).
The result all but mathematically dashed Rivoli's hopes of returning to the country's top flight next season, as they remain bottom of the four-team series with just one point, with two rounds of matches remaining.
Highgate, in the meanwhile, now have eight points, and a win at home over Seba United on Sunday's penultimate round could be enough to earn them their first taste of Premier League football.
Western Confederation champions Seba, for their part, also took a step closer - in their home encounter at Jarrett Park later in the evening - with a 2-1 win over Kingston and St Andrew Football Association champs Cavalier, that pushed them up to eight points and joint leadership.
Torrey Samuels (12th) and Omar Reid (70th) netted the goals for the Montego Bay team, while Lawrence Richards (90+) scored for the losers.
Early leaders Cavalier, in the meanwhile, remained second from bottom on four points, after suffering their second consecutive loss.