Hislop spent majority of his playing career in the top division in England where he was a part of the Newcastle United team which finished second in the Premier League for two successive seasons under Kevin Keegan's first tenure.
He later played for West Ham United on two occasions (receiving an FA Cup runners-up medal during his second season in 2006) and also for Portsmouth (where he won the First Division in 2002/03).
A dispute with the national team ruled him out of contention for several years, but he returned to play and starred in the country's first ever World Cup appearance in 2006.
[3] Shortly after graduating, Hislop was spotted by a scout from Reading at a friendly indoor match against Aston Villa of the Premier League.
He was instrumental in Reading's rise from the third tier of English football to the brink of the Premier League, where he narrowly missed out on promotion following a 4–3 defeat to Bolton Wanderers in the 1995 play-off final,[4] and was voted the club's Player of the Season in 1994–95.
[citation needed] Hislop's first season at Newcastle United was spent battling with incumbent goalkeeper Pavel Srníček for the starting role.
West Ham United had operated a "goalkeeper by committee" approach the previous season, seeing first Luděk Mikloško, then Craig Forrest, then Bernard Lama hold the starting role.
With Mikloško now with Queens Park Rangers and with the team being unable to secure Lama beyond his three-month loan, Harry Redknapp snapped up Hislop and installed him as first choice goalkeeper.
Hislop returned the following year in 2000–01 but in a tumultuous season, he saw his manager fired, and two of the club's most promising players in Rio Ferdinand and Frank Lampard sold on.
The deal was seen as a coup for West Ham, though it resigned Hislop to the bench for what was seen to be his final season with the club as James (a year younger) was intended to be the obvious long-term option.
Following the appointment of a new manager Alain Perrin, Hislop failed to regain his starting place in favour of ex-Liverpool keeper Sander Westerveld, and when his contract expired in June 2005, he was released by the club.
On 29 July 2005, Hislop rejoined West Ham as experienced cover along with Jimmy Walker for new signing Roy Carroll, allowing Stephen Bywater to go out on loan.
In January, Carroll's injury forced him to the physio's table once again, and Hislop stepped back into the fold as the starter (rotating with Walker).
On 10 June 2006, Hislop played in the Trinidad and Tobago national team's first ever World Cup match, a 0–0 draw against Sweden, replacing Kelvin Jack who suffered a calf injury in the warm-up.
[18] On 17 March 2009, Hislop signed a contract to be an assistant coach while primarily working with the goalkeepers of the Quinnipiac University football team.
In 2008, Hislop began a weekly blog covering Major League Soccer for the British newspaper The Guardian's website.
He works as a commentator on ESPN FC TV and in addition to commentary he has also interviewed several major footballing figures, including his former club manager Harry Redknapp after his move from Portsmouth to Tottenham Hotspur, USA international goalkeeper Kasey Keller, and Portuguese manager José Mourinho after he led Chelsea to the Premier League title in 2015.
On 10 July 2008, Hislop became the first member of the Trinidad and Tobago World Cup squad to be inducted into his country's Sporting Hall of Fame.