In 2008, Rodolph Austin lifted the Jamaica Premier League (JPL) title with Portmore United as a player. Almost two decades later, he lifted it again as head coach, leading the club to a record eighth top-flight crown.

Portmore dethroned Cavalier FC as champions of the Wray & Nephew JPL on Sunday at the National Stadium, prevailing 5-3 on penalties after a 2-2 draw following regulation and extra time.

Despite midfielder Ronaldo Robinson giving Portmore a fourth-minute lead, Cavalier looked on course to win their third-straight title after rising star Kimarly Scott responded with goals in the 26th and 42nd minutes to give them the advantage.

However, Tarick Ximines’ 60th-minute strike pulled Portmore level and ultimately sent the game into extra time and penalties, making it the third season in a row that the title would be decided from the spot.

After both teams scored their first three penalties, Portmore substitute Matthew Bell converted to make it four. But Cavalier substitute Terence Williams couldn’t do the same as his unique run-up and strike was saved by goalkeeper Daniel Russell.

Javier Brown would then smash home his penalty, enrapturing the St Catherine-based club and its supporters.

It was a feeling the club had missed for a while, as their last title win came in 2019. Portmore’s dip was seen after the COVID-19 pandemic, missing out on the play-offs in 2021, 2022 and 2023. They would return in 2024 and 2025, but failed to get past the quarter-finals in both years.

Former Reggae Boyz midfielder Austin, whose professional career started at Portmore in 2005, returned to the club as a player in 2022 after a 13-year stint in Europe.

However, he hung up his boots and was thrown into the fire as coach in September 2024 following the shock departure of Davion Ferguson.

At the time, Austin said his main objective was to see Portmore return to its glory days. With the mission accomplished, he’s proud of the history-making group.

“It’s a good feeling to get the club back where the club belongs and I’m happy for the players; they did really well throughout the season,” Austin told the Jamaica Observer.

“It’s been a roller-coaster season. Sometimes you have good times, sometimes you have bad times, but you just have to get the players together all the time because it’s football; it’s ups and downs and it’s like that.”

Austin, who competed at the highest levels of European football, including the English Championship and UEFA Europa League, is regarded as one of Jamaica’s most accomplished players, having won multiple Caribbean Cup titles with the Reggae Boyz, and played a key role in the nation’s historic run to the 2015 Concacaf Gold Cup final.

With this season’s championship success, his brief coaching career has already become one of the most decorated in the country. Still, Austin refuses to make the moment about himself.

“It’s good but I don’t dwell on those things. I’m more happy for the players,” he said.

“It’s not about me, it’s for the players. A lot of them haven’t won the Premier League before, and they get the chance to win it and they did that, and it’s all about them. The game is about the players.”

The win not only puts Portmore back to the pinnacle of Jamaican football but secured a return to regional football after qualifying for the Concacaf Caribbean Cup. The club won the now-defunct Caribbean Club Championship in 2005 and 2019.

Austin is looking forward to leading the team against the best in the Caribbean.

“That’s where the club wants to be and we have worked hard to try and get it there and we are here now so we have to just continue it,” he said.

“We just have to enjoy the night, enjoy the few days, and then we start to look towards that, get the team up and ready again.”

Cavalier, who were missing Head Coach Rudolph Speid, away with the Reggae Boyz in London for the Unity Cup, were unable to add to their four JPL titles.

However, Assistant Coach David Laylor isn’t overly disappointed, given their inexperience being the youngest team in the league.

“That’s football, mistakes win games and lose games at the end of the game; either you’re going to commit a mistake or your opponents will and we made a mistake in not concentrating on the defensive aspect of our game at that point,” he told the Jamaica Observer.

“[Although] we played against a good team, we believe we really could have won again, but it was not to be tonight. But, I’m just proud of the youngsters and the adjustments that they made coming from schoolboy football and transitioning into the Premier League.”

Despite the loss, Cavalier will compete in the Caribbean Cup for a fourth-straight year.

Portmore United players celebrate after beating Cavalier FC on penalties to win the Wray & Nephew Jamaica Premier League title on Sunday, May 24, 2026, at the National Stadium.(Photo: Naphtali Junior)

Portmore United supporters celebrate inside the grandstand of the National Stadium after seeing their team beat Cavalier FC in the final on Sunday,May 24, 2026. (Photo: Naphtali Junior)

Cavalier players react after the team lost on penalties to Portmore United in the final of the Jamaica Premier League on Sunday, May 24 at the National Stadium.(Photo: Naphtali Junior)

Cavalier’s Jeovanni Laing hurdles a challenge from Portmore United’s Matthew Bell during the final of the Jamaica Premier League, which was played at the National Stadium on Sunday, May 24 2026. Portmore United won 5-3 on penalties after a 2-2 scoreline at the end of regulation and extra time. (Photo: Naphtali Junior)

Portmore United coach Rodolph Austin pointing to his players after winning the Wray & Nephew Jamaica Premier League title. (Photo: Naphtali Junior)