Big Five 24: ‘Caps’ clinch title, ex-Shiva Boys coach leads Scarborough to history—in dramatic finale

Scarborough Secondary are a Secondary Schools Football League (SSFL) Premier Division team for the first time, as they were one of three schools who clinched promotion on the last day of the 2024 SSFL Big Five competition today.

Scarborough needed a point at the St Mary’s Recreation Ground in Freeport against leaders Carapichaima East Secondary, and they got it—in a tense 1-1 draw. The result did not deny “Caps” the Big Five title, as they finished top of the table.

Carapichaima East Secondary captain Darion Boswell (left) stabs the ball away from Scarborough Secondary forward Jayden Pope during SSFL Big 5 action at the St Mary’s Recreation Ground in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

And, across in Marabella, Trinity College (Moka) also booked their place in the 2025 Premier Division season with a 2-2 draw away to Pleasantville Secondary.

Hillview College missed out, though. The East Zone Championship winners started the day in third place, with the top three schools certain to advance. And, as the results swung back and forth, Hillview still appeared to be Premier Division-bound until roughly 5pm when Scarborough substitute Jesuron “Sick” Woods got the most important goal of his young career so far.


“What does promotion mean for you, and for Scarborough Secondary?” Wired868 asked Ryan, who won the Premier Division and National Intercol titles as coach at Shiva Boys Hindu College in 2016 and 2017 respectively.

Ryan opened his mouth, but the response was not a verbal one. Inadvertently, the tears came instead as he turned and moved away from his players—trying to regain his composure.

Scarborough Secondary coach Hayden Ryan (centre, yellow jersey) makes a point while fourth official Rodphin Harris (right) watches on during SSFL Big 5 action at the St Mary’s Recreation Ground in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

It took a minute before he could try to answer directly, and, even then, his voice crackled with emotion as he spoke.

“It means a lot,” said Ryan. “It is not just for the school but for football on the whole. We were able to take guys who don’t even believe in themselves—some of them who didn’t even think they could be footballers—and groom them into this.

“I want to give God thanks and praise.”

The St Mary’s Recreation Ground in Freeport was an unlikely venue for SSFL football history. Uneven with three big dirt patches and grass that looked about three inches long in some areas.

The St Mary’s Recreation Ground in Freeport hosted a crucial SSFL Big 5 matchup between Carapichaima East Secondary and Scarborough Secondary on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

Both schools knew they needed a draw to advance—and both could face another year in the Championship Division with a defeat. (Carapichaima East would finish fourth with a 3-0 loss, while any defeat spelt doom for Scarborough.)

“Remember, today is the day!” Scarborough manager and teacher Nicole Williams-Wilson roared, as her boys strode out onto the field for kickoff.

“Not bad, lads!” Carapichaima coach Jaeel Jeffrey shouted to his players, as they bounced rhythmically—awaiting the opening whistle from referee Nathalya Williams. “I like what I’m seeing already!”

The Carapichaima East Secondary team pose before kickoff against Scarborough Secondary in a Big 5 fixture in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

In truth, there was more perspiration than inspiration in the first half. Scarborough’s tactics were to kick the ball as far upfield as possible and see if forward Jayden Pope could make gold from straws. Carapichaima were a bit more expansive in possession but could not seem to get a shot on target for love or money.

Scarborough had two hopeful penalty shots. They claimed a handled ball by opposing midfielder Jerel Charles while Carapichaima defended an inswinging corner kick in the 13th minute. And there were appeals when Caps captain and central defender Darion Boswell took boy (Jervae Weekes) and ball with a crunching tackle in the 40th minute.

On each occasion, the referee was not suitably convinced.

Referee Nathalya Williams oversees Big 5 action between Carapichaima East Secondary and Scarborough Secondary in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

Carapichaima had an excellent chance to go ahead in the 31st minute after opposing captain Johan Elliot needlessly lost possession dribbling near the half line.

Damarion Boswell, the captain’s younger brother and Carapichaima’s playmaker, relayed the ball to Raykan Roberts, whose superb right side cross was headed inches wide by forward Teriq Langton—with Scarborough goalkeeper Jaden Gilman stranded.

In the 44th minute, Scarborough left back Christian Winchester with a goal line clearance after Caps full back Mikael Aberdeen headed down a Keon Kissoon corner kick.

Carapichaima East Secondary goalkeeper Jayden Meharris passes on instructions to his defence during SSFL Big 5 action against Scarborough Secondary at the St Mary’s Recreation Ground in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

At the interval, it was goalless in Freeport. In Marabella, Pleasantville led Trinity 1-0.

If the scores remained as they were, Carapichaima, Scarborough and Hillview would qualify in that order; and Trinity would be out.

Ryan spent much of the interval imploring his players to remain calm, focused and vigilant. Then they went back out and promptly conceded a soft goal.

Scarborough Secondary players take a snap before kickoff in their closing Big 5 clash with Carapichaima East Secondary in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

Scarborough play route one football at the start of their build-ups with their players having license to dingolay on the ball once they get possession in the opposing half of the field.

But it is also worth mentioning that Pope, their slender centre forward, was repeatedly smothered by the Caps central defensive pairing of Darion Boswell and Shemo John.

In the 48th minute, the Scarborough goalkeeper, Gilman, left-side central defender Daniel Walters, and left back, Winchester, decided to try something else.

Carapichaima East Secondary captain and defender Darion Boswell (left) steals the ball from Scarborough Secondary forward Jayden Pope during SSFL Big 5 action at the St Mary’s Recreation Ground in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

They probably still are not sure what that was exactly. But the end result was they traded about four passes between each other on the edge of their own penalty area—each seemingly expecting the other to figure something out—before Damarion stole the ball and blasted home the opening goal.

Caps were ahead. And, if the score stayed like that in Freeport, the host team would lead Hillview and Trinity into the Premier Division.

It would be an understatement to say the Scarborough coach was upset.

Carapichaima East Secondary midfielder Damarion Boswell (centre) blasts home the opening goal while Scarborough Secondary defenders Christian Winchester (left) and Daniel Walters watch on during SSFL Big 5 action at the St Mary’s Recreation Ground in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

“Gillie, why you played that ball short?!” Ryan was still asking his goalkeeper, during a break in play—an entire three minutes later.

Carapichaima looked more relaxed now and were even stroking the ball about at times, with Damarion and Charles proving too much for talented 15-year-old Scarborough midfield playmaker Amari Allie Baccas.

Baccus, incidentally, turned 15 today. But Carapichaima had no gifts for him.

Scarborough Secondary midfielder Amar Allie Baccas (centre) tries to keep the ball from Carapichaima East players Jerel Charles (left) and Teriq Langton during SSFL Big 5 action at the St Mary’s Recreation Ground in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

Scarborough, who lost on their last Big Five outing in Trinidad against Pleasantville, were in trouble.

Ryan turned to 14-year-old flanker, Woods, who entered the field in the 60th minute for the burly Kaniel Davidson. Woods, or “Sick”—as his teammates called him—might have been introduced sooner, but fourth official Rodphin Harris noticed that he was preparing to go on without shinpads and waved him back to his bench.

Really, fellah? Do you think this is a sweat?

Carapichaima East Secondary supporters sense triumph during their SSFL Big 5 clash with Scarborough Secondary at the St Mary’s Recreation Ground in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

In the 69th minute, Caps almost extended their lead as Walters misjudged a defensive header, which was then fumbled on to the Scarborough bar by Gilman.

Elsewhere in Marabella, Pleasantville were reduced to nine players as Jahiemn Phillip and Jelani Roberts were sent off for violent conduct in the 63rd minute—as referee Cecile Hinds saw the duo throw punches during a flareup between the two teams.

And, in the 71st minute, Jaden Samuel equalised for Trinity against the short-handed “P-ville”. At 1-1, the North Championship winners were safe regardless of what happened in Freeport.

Scarborough Secondary midfielder Johan Elliot (right) tries to wriggle free from Carapichaima East midfielders Jerel Charles (centre) and Kamarli Wilson during SSFL Big 5 action at the St Mary’s Recreation Ground in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

Hillview needed Carapichaima to stay up though.

Then, from nothing more than a speculative lofted pass into the area, danger showed up. Woods gambled, as he left the right flank and dashed into the box in search of scraps, and was in the right place at the right time.

He lifted the ball over opposing goalkeeper Jayden Meharris, and the sphere seemed to hang in the air for an eternity before it drifted under the bar and nestled into the back of the net.

Sick one!
Scarborough Secondary substitute Jesuron “Sick” Woods (centre) is congratulated by teammates for his crucial equaliser against Carapichaima East in SSFL Big 5 action at Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

Scarborough players erupted. And Hillview might have felt Sick.

“Who was that?!” a beaming Ryan asked his bench, with an incredulous look. “Woods?!”

Carapichaima threatened with a couple of wicked inswinging corner kicks by Kissoon and Damarion. But the defiant Gilman refused to be beaten a second time.

Carapichaima East Secondary midfielder Damarion Boswell routinely worried Scarborough Secondary from corner kicks during their SSFL Big 5 clash in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

It might have gotten better still for Scarborough in the last minute of stoppage time, as Pope finally twisted himself free of his markers—only to be tripped at the edge of the area.

Williams whistled for a free kick, just as the loose ball rolled to Pope’s teammate, Weekes, who was free as a bird in the box with only Meharris to beat.

Ryan held his head in his hands and dropped to his knees.

Scarborough Secondary coach Hayden Ryan (left) barks instructions from the sideline during his team’s clash with Carapichaima East Secondary in SSFL Big 5 action at the St Mary’s Recreation Ground on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

“Why yuh didn’t give we the advantage, ref?!” he moaned.

But Scarborough had made their point. And they followed Carapichaima upstairs.

“We wanted to begin the year on a winning note but that wasn’t the case,” said Carapichaima coach, Jeffrey. “But we are thankful all the same for the promotion.”

Carapichaima East Secondary coach Jaeel Jeffrey (left) passes on orders to his players during their SSFL Big 5 fixture against Scarborough Secondary in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

Trinity were 2-1 ahead against the nine-man Pleasantville team, as Carapichaima players began their cool-down exercises. The final day results, as they stood, meant that the North Zone school had won the competition.

A former top flight coach with Chaguanas North Secondary, Jeffrey believes he knows what Caps need to be successful in the Premier Division and is looking forward to getting his squad into shape during the preseason.

He credited his boys for getting a result in “difficult circumstances” today, which saw them finish their Big Five campaign unbeaten—along with Trinity.

Carapichaima East Secondary midfielder Jerel Charles (left) looks for a passing option during SSFL Big 5 action against Scarborough Secondary at the St Mary’s Recreation Ground on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

“For the most part, I thought we controlled the game—but we just didn’t take our chances,” said Jeffrey.

He was charitable to their guests too and dismissed any suggestion that they were fortunate to get a point.

“I wouldn’t say they were lucky,” said Jeffrey. “They took their chance. That is how the game goes sometimes.”

Scarborough Secondary forward Jayden Pope (foreground) tries to control the ball under pressure from Carapichaima East Secondary captain Darion Boswell during SSFL Big 5 action at the St Mary’s Recreation Ground on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

Carapichaima East, the Central Zone’s most successful school of the Premier Division era, were never going to remain in the second tier for too long. If anything, the surprise is that it took them two seasons to plot a return to the top flight.

But Scarborough? That’s another story entirely.

Ryan’s star burnt bright and brief in the Premier Division. After inheriting the Shiva Boys job from coach Dexter Francis, Ryan won the Premier Division, South Zone Intercol and National Intercol title in two seasons—and then they were demoted for fielding a player, Matthew Beal, who voided his own registration by playing in a South Zone FA match.

Calm down Coachman! Shiva Boys HC players Yohannes Richardson (left) and Tyrel “Pappy” Emmanuel (centre) successfully petition coach Hayden Ryan as he considers making a substitution during the South Zone Intercol final against Presentation College (San F’do) at the Mannie Ramjohn Stadium in Marabella.
Shiva Boys won 2-0.
Photo: Chevaughn Christopher/ Wired868

Shiva Boys scrapped their football programme and Ryan disappeared from sight.

In 2023, Ryan visited Scarborough Secondary to sell jerseys to the school’s football team.

“I sell sublimation jerseys: round neck and polo,” he said. “I just went there looking for business.”

Scarborough Secondary captain Johan Elliot tries to control the ball during SSFL Big 5 action against Carapichaima East Secondary at the St Mary’s Recreation Ground in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

He couldn’t help but mention to team manager and teacher Nicole Williams-Wilson that he was able to offer more skills to the Scarborough football programme, if they were interested.

“I mentioned to them that I am a football coach,” said Ryan, “and when they asked my name and I told them, they said they heard about that name already.

“So, I told them if they need a coach I am here. And I promised them: give me two years and I will take you to the premiership!”

Scarborough Secondary coach Hayden Ryan celebrates at the St Mary’s Recreation Ground on 21 January 2025, as his team booked promotion to the Premier Division with a 1-1 draw with Carapichaima East Secondary.
Photo: Nicholas Bhajan/ Wired868

Midway through the 2023 season, Scarborough offered Ryan the job as head coach. Since then, he has moved between the two islands—staying at an apartment for a few days in Tobago to train the team before flying back to Vistabella.

“It is a helluva story,” said Ryan, with a smile.

As the players stretched at the sidelines, a roar went up from the Carapichaima East players. News emerged of a last-minute leveller in Marabella.

Pleasantville pegged Trinity College back 2-2. And Carapichaima were the 2024 Big Five champions, on goal difference!

Carapichaima East Secondary players offer coach Jaeel Jeffrey a drink in Freeport on 21 January 2025, after discovering that they had clinched the SSFL Big 5 title.
Photo: Nicholas Bhajan/ Wired868

The Big Five was finally over. For Carapichaima East, Trinity and Scarborough, it was worth the wait.

Teams

Carapichaima East Secondary (4-3-3): 1.Jayden Meharris (GK); 12.Keilon Forde, 23.Shemo John, 24.Darion Boswell (captain), 11.Mikael Aberdeen; 10.Damarion Boswell, 8.Jerel Charles, 9.Kamarli Wilson; 7.Keon Kissoon, 17.Teriq Langton, 5.Rayhan Roberts.

Unused substitutes: 18.Liam Alleyne (GK), 2.Zephan Babb, 3.Justyn Charles, 4.Gary Samaroo, 13.Derwin Francis, 14.Christiano Lively, 15.Nkosi Yorrick, 16.Kalen Sandiford, 20.Jawwad Hypolite.

Head coach: Jaeel Jeffrey

Scarborough Secondary (4-1-4-1): 1.Jaden Gilman (GK); 3.Khadeem Phillips, 18.Daniel Walters, 10.Jaheim Toney, 20.Christian Winchester; 6.Johan Elliot (captain); 17.Zoevanni Baird, 12.Kaniel Davidson (21.Jesuron Woods 60), 8.Amar Allie Baccas, 9.Jervae Weekes; 11.Jayden Pope.

Unused substitutes: 16.Nico James, 19.Izaiah Wilson, 23.Ajay Stewart, 24.Izea Phillip.

Coach: Hayden Ryan

Referee: Nathalya Williams

Carapichaima East Secondary scorer Damarion Boswell (centre) celebrates his goal with teammates Kamarli Wilson (left) and Jerel Charles during their SSFL Big 5 clash with Scarborough Secondary at the St Mary’s Recreation Ground on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

SSFL Big Five results

(Tue 21 Jan)

Pleasantville Secondary 2 (Javelle Williams 12, Ajahidi Noray 90+6), Trinity College 2 (Jaden Samuel 71, Jashon Forde 88) at Mannie Ramjohn Stadium Training Field;

Carapichaima East Secondary 1 (Damarion Boswell 48), Scarborough Secondary 1 (Jesuron Woods 75) St Mary’s Recreation Ground.

Scarborough Secondary playmaker Amar Allie Baccas (foreground) tries to create room for himself during SSFL Big 5 action against Carapichaima East Secondary in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

Standings (Played-Won-Drew-Lost-Goals For-Goals Against-Points)

Carapichaima East      4-1-3-0-5-36

Trinity College             4-1-3-0-5-4-6

Scarborough Sec          4-1-2-1-6-5-5

Hillview College           4-1-2-1-4-4-5

Pleasantville Sec           4-0-2-2-372

Scarborough Secondary attacker Zoevanni Baird (right) tries to find a way around Carapichaima East Secondary defender Mikael Aberdeen (centre) and goalkeeper Jayden Meharris during SSFL Big 5 action in Freeport on 21 January 2025.
Photo: Nicholas Bhajan/ Wired868

Scorers

2—Kemarley Pierre (Hillview College), Antonio Cole (Trinity College),

1—Jerel Charles, Teriq Langton, Kamarli Wilson, Darion Boswell, Damarion Boswell (Carapichaima East), Khadell Campbell (pen), Tefari Kerr (Hillview College), Jelani Roberts, Javelle Williams, Ajahidi Noray (Pleasantville Secondary), Tyrese Neptune, Jayden Pope, Jahiem Toney, Johan Elliott, Jervae Weekes, Jesuron Woods (Scarborough Secondary), Anton Joseph, Jaden Samuel, Jashon Forde (Trinity College),

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