[3] He made his Jersey debut in the annual 50-over Inter-Insular Cup match against Guernsey on 31 August 2019, scoring 53 in a five-wicket win.
[4][5] In September 2019, Greenwood was named in Jersey's Twenty20 International (T20I) squads for the series against Qatar and the 2019 ICC T20 World Cup Qualifier tournament in the United Arab Emirates.
[14] During the 2024 Men's T20I Inter-Insular Series against Guernsey, Greenwood registered the highest individual score of the competition, smashing 85 off 50 balls, including three sixes and nine fours, in the opening match to help Jersey to a 2–1 win.
[15][16] In the opening match of the 2024–25 ICC Men's T20 World Cup Europe Qualifier in Germany in July 2024, Greenwood made 85 not out against Serbia as Jersey scored their highest T20I total to date, racking up 233 for 3.
[18] Greenwood took his first five-wicket haul in List A cricket in the islanders' match against Qatar, bagging a player-of-the-match winning 5/38 in a 168-run victory.