Hamilton made his first-class debut at the age of 17, playing for Leeward Islands against Barbados in 2008. Four years later, he was selected for a one-year training programme at the West Indies High Performance Centre in Barbados. In 2013, Hamilton was included in the now-defunct Antigua Hawksbills squad for the inaugural Caribbean Premier League edition. He played only one match that season and didn't play another T20 for the next six years.

In 2016-17, Hamilton was the third-highest scorer in the regional four-day competition with 648 runs at an average of 46.28. But it wasn't until 2018 that he came into the reckoning for the national side. That year, he impressed for West Indies A with the scores 100, 29 and 79 against a touring England Lions side in the two first-class matches. As a result, he was selected as one of two wicketkeepers alongside Shane Dowrich for the home Test series against Sri Lanka.

Later that year, he travelled to India and Bangladesh as well with the Test side but Dowrich's presence meant he didn't get a chance to play. Hamilton eventually made his Test debut in 2019, against India in Kingston when injuries to Dowrich and Shai Hope ruled them out for the match.
Hemant Brar