The all-Caribbean clash also marked the tournament's first game at the Estadio Cuauhtemoc, home to Liga MX-side Puebla. Mexico is scheduled to meet Curacao at the same venue later in the evening.
Jamaica took the lead in the eighth minute, when Omar Holness swooped in to score after Paul Wilson's initial shot was saved by goalkeeper Matthew Sanchez.
Despite conceding early, Puerto Rico regrouped and bounced back quickly.
A long free kick in the 22nd was played into the Jamaican box by Gustavo Rivera. Puerto Rico's Emmanuel D'Andrea and defender Alvas Powell crashed into each other contesting a header. The ball came loose and Reid Strain pounced to level the score. Only minutes earlier, Strain was being receiving mediacal attention off the field after sustaining a bloody nose from a collision.
The young Reggae Boyz were not deterred by the setback and resumed their attacking ways without hesitation. Over the next 23 minutes, they had four quality scoring opportunities.
Zhelano Barnes offered the best one in the 37th minute, as his free kick from 18-yards out deflected off the and struck the right post.
While Puerto Rico was able to withstand the first-half pressure, it could not replicate that performance in the second stanza. The Jamaicans kept to their game plan, continually attacking with numbers from many different areas of the field.
Damion Lowe, son of former Jamaican national team star Onandi Lowe, put Jamaica ahead for good in the 61st minute, right-footing home a Holness corner kick minus the slightest of challenges.
With 20 minutes left on the clock, Anderson netted the first of his two goals, heading in an Andrew Lewis cross from only four yards out.
Anderson completed the score line, running onto a ball that bounced over the Puerto Rican central defense and calmly sliding his attempt past Sanchez.
Alex Oikkonen nearly pulled one back for Puerto Rico in the 89th, forcing a save at full stretch from Jamaican goalkeeper Rashaun Patterson.
Jamaica returns to action on Saturday against Panama, while Puerto Rico will face the Central American side on Thursday.