*Club domestic league appearances and goals, correct as of 17:10, 22 May 2024 (UTC) ‡ National team caps and goals, correct as of 5:00, 7 September 2024 (UTC)
On 4 February 2017, Charles-Cook joined National League side Solihull Moors on loan for the remainder of the campaign.[3] A week later, during his debut for Solihull, Charles-Cook scored twice against Sutton United in their 3–0 victory.[4] On 17 April 2017, Charles-Cook sealed Solihull Moors' 3–1 away victory against Macclesfield Town, netting the third goal in the 93rd minute.[5] Charles-Cook returned to Charlton following the conclusion of the campaign, in which he scored four times in thirteen games.
Following an impressive loan spell with Solihull, Charles-Cook returned to Charlton for the 2017–18 pre-season. He scored his first goal for Charlton in a 2–1 EFL Cup win against Exeter City on 8 August 2017.[6]
On 1 September 2017, Charles-Cook joined Woking on loan until January 2018.[7] A day later, Charles-Cook made his Woking debut during their 3–1 away victory against Macclesfield Town, replacing Jason Banton in the 60th minute.[8] On 16 September 2017, Charles-Cook scored both goals in Woking's 2–0 home victory over local rivals, Sutton United.[9] In January 2018, Charles-Cook returned to Charlton after sustaining a long-term ankle injury whilst at Woking. On 8 March 2018, Charles-Cook rejoined Woking on loan until 28 April 2018.[10] A day later, he marked his return, assisting Charlie Carter for his tenth goal of the season in Woking's 3–1 home defeat against F.C. Halifax Town.[11]
Gillingham
Charles-Cook reportedly signed a new one-year contract with Charlton at the end of the 2017-18 season,[12] however shortly afterwards he signed for Gillingham on 30 May 2018.[13]
Ross County
On 30 June 2020, Charles-Cook joined Scottish Premiership club Ross County.[14] He struggled in his first season, with him citing homesickness and not being able to visit his family due to COVID-19 restrictions as factors, and was in and out of the team.[15] His second season saw him become a regular in the side under new manager Malky MacKay,[15] with his improved form seeing him linked with moves to Aberdeen and Hibernian.[16] On 28 January 2022, he scored one of Ross County's goals in a 3–3 draw with Rangers, making him at the time the top goalscorer in the Scottish Premiership on 10 goals.[17]
On 1 July 2021 Charles-Cook was called up to Grenada's squad for the 2021 CONCACAF Gold Cup.[19] He started all three matches as Grenada exited at the group stage, making his debut in the side's opening game of the tournament, a 4–0 defeat to Honduras.[20]