Anguilla Football League
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Uprising FC
2026-05-15 

Meet Darlon Guppy: Uprising FC’s Ambitious Trinidadian Defender

You may have noticed recently that we have made no fewer than four new signings from Trinidad & Tobago. All four lads have settled in very well into the Uprising Family, and having done so, we thought it was a good time to catch up with them to find out more about their careers to date and their thoughts on playing for our club. Having already interviewed Isaiah Isaac in episode one of this four-part series, episode two sees us talking to Darlon Guppy.

Darlon Guppy – Summary of his Life:

Born in 2001, Darlon has travelled a football journey that reflects resilience, determination, and ambition. The nephew of former Trinidad & Tobago international Curtis Ravello, who inspired Darlon to play football and naturally became a major influence in his life, Darlon began playing football at the tender age of four years old. Over time, he has developed into a versatile player who plays mainly as a centre-back and midfielder.

Over the years, Darlon has played for several respected clubs and academies across his native Trinidad & Tobago; including Sky FC, Central FC, Caledonia AIA, Santa Cruz United Academy, and Lambenthal United FC. In addition to this, Darlon’s talents were recognised during his educational studies when he played for San Juan South Secondary and later at Queen’s Royal College.

Upon finishing High School, Darlon received a partial scholarship to attend Angelina College in Texas, but personal circumstances prevented him from doing so. Nonetheless, he continued to pursue international opportunities; training in Mexico, travelling to Portugal for trials, and later joining a development camp in Costa Rica.

His career has not been without challenges which include cancelled opportunities during COVID-19, contracting the virus whilst in Portugal, and injuries, and personal hardships. However, he has used these difficult periods to improve himself academically and has earnt certifications in Physiotherapy, CPR, Even Management, and Fitness Instruction.

In terms of football, a major breakthrough for Darlon came in 2023 when he trained with the Soccer Visa FC Development Centre in Costa Rica and subsequently signed for a Romanian club called Club Athletic Oradea, making his European football debut in September 2023!

Beyond football, Darlon is an active member of his community in Trinidad & Tobago by mentoring younger players and hosting football camps. His story to date shows perseverance, faith in God, and a willingness to take risks. He also has a strong desire to one day represent Trinidad & Tobago at international level!

Interview:

Darlon is close friends with Uprising FC player and fellow Trinidadian Joel Orosco which is what first attracted him to join our club. As Darlon explained, this was one of the factors in his decision to join us.

“I wanted a new challenge, and with me being friends with Rosco, I did my research on Anguilla and found out that it is a very peaceful island which made my mind up to leave Trinidad & Tobago. I saw that I could strengthen the side and help my new teammates, because my aim is to win the league with the club!”

Darlon has had great experiences over the years during his football journey, and as he is a new signing for us, we asked him how he would describe himself as a player.

“I am a leader, who is very vocal in the defensive line. My best attributes are winning aerial duels, and I would describe myself as a ball playing/ball winning centre back who can break lines and come out of any situation!”

As Darlon previously said, he strongly believes that we can win the league this season which is of course music to the ears of everyone connected to Uprising FC! In his own words he told us; “If we don’t, then it is because of us, so we have to give everything on the pitch!”

It is clear to see that our new Trinidadian centre back is a very determined and ambitious player, and on that note, we asked him to tell us his short term and long-term ambitions.

“Short term is to continue fighting game by game to achieve 3 points for the team every time we take to the field. My long-term ambitions are to win the title and do well both on and off the field. I want to show that I came here on a mission and want to prove that I am not just a footballer and that I am also someone who wants to contribute to society.”

To finish, Darlon shared his thoughts on his time in Anguilla thus far.

“So far, I am loving it! Anguilla is ME! What I mean by that is I am at peace in life and this island is full of peace, I love it!”

We are delighted to have Darlon on board at our club and we look forward to a promising future with this energetic, ambitious, and determined individual.

 

Interview – Gareth Thomas: Media Officer/Assistant General Secretary for Uprising FC.

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