Despite many not viewing Cavalier FC as a favourite to win the Wray & Nephew Jamaica Premier League title this season, Assistant Coach David Laylor says the team always believed they would be in the hunt for top honours again.

The two-time reigning champions booked their spot in Sunday’s semi-final against Montego Bay United after their 2-0 second-leg quarter-final win over Waterhouse on Wednesday at the National Stadium, to advance 4-2 on aggregate.

Dwayne Allen in the 29th and talisman Christopher Ainsworth in the 79th minute got the job done for Cavalier, who scored four unanswered goals over the two matches, after falling 0-2 behind in the first leg.

Although they failed to beat Waterhouse in their previous six matches, Laylor says they were confident that the seventh time would be different.

“The boys really believed it and the coaches believed it too that we were at least two goals better than them because they were two goals up and we got two goals coming back, so if we shut them out then we should be able to score at least a goal or two and that was just it,” he said.

Cavalier lost several of last season’s star players including Reggae Boyz Richard King, Dwayne “Busy” Atkinson and Jalmaro Calvin.

With Rudolph Speid’s club in a rebuilding phase, Cavalier were unable to retain their Concacaf Caribbean Cup crown and hovering midtable in the JPL regular season, as low as eighth at one point.

However, they finished the season strong, picking up 16 points from a possible 21 in their last five games, which saw them finish fifth, though it was their lowest league placing in four years.

While Mount Pleasant Football Academy and Montego Bay United have gotten most of the plaudits this season, Laylor believes his side shouldn’t be counted out.

“For those who doubt Cavalier, I don’t know why they would doubt Cavalier,” he said. “We are last year’s champions and before that too. Whenever we reach the playoffs, they get a different level of football, a different level of intensity so at the end of the day, we are here for keeps.”

Cavalier will look for their fourth title in five years but Waterhouse’s 20 year drought continues.

In January, Argentine Javier Ainstein replaced long-time Head Coach Marcel Gayle — who was also on the Cavalier bench as an assistant — and was tasked with leading the club to the summit.

Ainstein is uncertain if his four month stay in Jamaica will extend into next season.

“Maybe,” he said. “Always in football you need to be cautious. I have a contract but you never know what is for the future.”

“I know that during the season all the expectations grew but in these two matches we just play 20 minutes, 20 minutes, 20 minutes, 20 minutes. For me, my pain is that we finished without order on the pitch and this is the difference between Cavalier and us.”

Midfielder Omani Leacock says the Drewsland club has a lot to learn if they are to challenge for the title in the future.

“Honestly I think we didn’t play our style of play that we usually play. I think we struggled and I can say it’s down to the boys’ experience at this level,” he said.

“They are not accustomed to playing at this level. Maybe next year we can come again and learn from this moment, continue being us and don’t change because of the atmosphere or the fans.”

Chad James of Cavalier (left) comes under pressure from Watherouse’s Kvist Paul during the second leg of the Jamaica Premier League play-off at the National Stadium on Wednesday, May 13, 2026. Cavalier won the match 2-0 to advance 4-2 on aggregate. They will face Montego Bay United in the semi-finals on Sunday. (Photo: Garfield Robinson)

Cavalier’s Christopher Ainsworth (centre) celebratres with teamates and fans after scoring in his team’s 2-0 win over Waterhouse in the second leg of their quarter-finals playoff at the National Stadium on Wednesday, May 13, 2026. (Photo: Garfield Robinson)