The 21-year-old was a regular for Jamaica's U-17 and U-20 men's national teams, and has featured in senior national team squads in recent years, but has yet to win a full international cap for his country. Flemmings was named to the 40-man preliminary roster for the 2017 Gold Cup by the Reggae Boyz - one of several young or uncapped players on that list.
It would appear Flemmings will get the opportunity to make his senior national-team debut at Caribbean Cup in Martinique. The tournament runs from June 22 to June 25. Final Gold Cup rosters must be confirmed to CONCACAF by June 27.
Jamaica has dominated Caribbean Cup recently, winning four of the last six titles, including the last tournament in 2014. The four teams in the final rounds of the 2017 edition face a quick-fire warm-up for Gold Cup - a competition for which they are all also qualified. The 2017 Caribbean Cup will be staged in Martinique. The host nation will play Curacao on June 22, with Jamaica playing French Guiana on the same day. The winners of those two games advance to the final on June 25; losers play a third-place playoff the same day.
As such, Jamaica is guaranteed two competitive matches against opponents also keeping one eye on the CONCACAF championship that starts on July 7. It is not expected that all - or even most - of the players summoned to Caribbean Cup by the Reggae Boyz will feature in Gold Cup. The senior players on the Gold Cup roster - such as Philadelphia Union 'keeper Andre Blake and RBNY defender Kemar Lawrence - aren't playing in Martinique. But the CFU championship does provide Jamaica head coach Theodore "Tappa" Whitmore with a chance to look closely at emerging players, with a view to seeing a few push themselves into the reckoning for places in the Gold Cup squad.
Flemmings is some distance down the Jamaica depth chart at his position, though it remains to be seen how Whitmore thinks the player - a schoolboy soccer scoring legend in Jamaica - fits into the senior team's tactics and plans. In the current squad, one would currently consider forwards Cory Burke, Shamar Nicholson, and Jermaine Johnson to be ahead of Flemmings in Whitmore's thoughts, based on the pattern of recent Reggae Boyz squads and lineups.
The Jamaica squad for the 2017 Caribbean Cup in full, per the Jamaica Observer:
Dwayne Miller (Syrianska FC), Damion Hyatt (Arnett Gardens FC), Rosario Harriott (Harbour View FC), Damion Lowe (Tampa Bay Rowdies), Ladale Ritchie (Montego Bay United), Oniel Fisher (Seattle Sounders), Sergio Campbell (Pittsburgh Riverhounds), Jamie Richardson (UWI FC), Ewan Grandison (Portmore United), Cory Burke (Bethlehem Steele), Michael Binns (Portmore United), Shaun Francis (San Jose Earthquakes), Jermaine Johnson (Tivoli Gardens FC), Kevon Lambert (FC Vojvodina), Shamar Nicholson (Boys' Town FC), Ricardo Morris (Portmore United), Javain Brown (Harbour View FC), Shaun Genus (Reno FC), Junior Flemmings (NY Red Bulls II), Owayne Gordon (Montego Bay United).