This is a list of participation by football clubs in the Cayman Islands in North American competitions.
In 1981, Yama Sun Oil became the first Caymanian football club to participate in a CONCACAF competition, entering in the Caribbean zone of the 1981 CONCACAF Champions' Cup. They advanced to the second qualifying round before losing to SUBT of present-day Curaçao.
See main article: CONCACAF Champions Cup.
| Season | Team | Round | Opponent | Home | Away | Aggregate | ||
|---|---|---|---|---|---|---|---|---|
| 1981[1] | Yama Sun Oil | First round | St. Thomas | 1–0 | 1–0 | 2–0 | ||
| Second round | SUBT | 1–2 | 0–5 | 1–7 | ||||
| 1984[2] | Saint George's | Results unknown | ||||||
| 1991[3] | Strikers | First round | Racing Gonaïves | 0–0 | 1–2 | 1–2 | ||
| 1992[4] | Strikers | First round | Aiglon | 0–0 | 0–7 | 0–7 | ||
See main article: CONCACAF Caribbean Cup and CFU Club Championship.
| Season | Team | Round | Opponent | Home | Away | Aggregate | |
|---|---|---|---|---|---|---|---|
| 2002 | George Town | Preliminary round | Harbour View | 0–3 | 1–7 | 1–10 | |
| 2010 | Elite | Withdrew | |||||
| 2011 | Bodden Town | Preliminary round | River Plate | 1–0 | 0–2 | 1–2 | |
| 2012 | Elite SC | Group 1 | George Town | 1–2 | — | 2nd | |
| North Village Rams | 2–1 | — | |||||
| George Town | Group 1 | Elite | 2–1 | — | 1st | ||
| North Village Rams | 0–0 | — | |||||
| Group 4 | Caledonia AIA | 0–5 | — | 3rd | |||
| Puerto Rico Islanders | 0–8 | — | |||||
| 2014 | Bodden Town | Group 1 | Bayamón | 0–5 | — | 4th | |
| Centro Dominguito | 2–4 | — | |||||
| USR | 0–1 | — | |||||
| 2016 | Scholars International | Group 1 | Central | 0–6 | — | 3rd | |
| Montego Bay United | 0–4 | — | |||||
| 2017 | Elite | Group A | Barcelona Atlético | 0–4 | — | 4th | |
| Grenades | 0–2 | — | |||||
| Montego Bay United | 0–5 | — | |||||
| Scholars International | Group D | Portmore United | 0–2 | — | 4th | ||
| Puerto Rico FC | 0–4 | — | |||||
| Transvaal | 0–4 | — | |||||
See main article: CONCACAF Caribbean Shield.
| Season | Team | Round | Opponent | Home | Away | Aggregate | |||
|---|---|---|---|---|---|---|---|---|---|
| 2018 | Bodden Town | Group C | Cayon Rockets | 2–1 | — | 3rd | |||
| Centro Dominguito | 0–0 | — | |||||||
| Franciscain | 2–5 | — | |||||||
| 2019 | Scholars International | Group A | Fruta Conquerors | 2–0 | — | 3rd | |||
| Jong Holland | 0–1 | — | |||||||
| Santiago de Cuba | 0–0 | — | |||||||
| Consolation round | Dakota | — | 1–2 | 1–2 | |||||
| 2020 | Scholars International | Group B | Inter Moengotapoe | — | |||||
| Metropolitan | |||||||||
| Santiago de Cuba | |||||||||
| 2022 | Scholars International | Group A | Bayamón | Withdrew | |||||
| Junior Stars | |||||||||
| South East | |||||||||
| 2023 | Scholars International | Group B | Golden Lion | style="text-align:center;" | — | style="text-align:center;" | 0–4 | 2nd | |
| South East | style="text-align:center;" | 2–0 | style="text-align:center;" | — | |||||
| Waterhouse | style="text-align:center;" | 3–0 | style="text-align:center;" | — | |||||
| Team | |||||||
|---|---|---|---|---|---|---|---|
| Strikers | 4 | 0 | 2 | 2 | 1 | 9 | −8 |
| Yama Sun Oil | 4 | 2 | 0 | 2 | 3 | 7 | −4 |
| Total | 8 | 2 | 2 | 4 | 4 | 16 | −12 |
| Team | ||||||||
|---|---|---|---|---|---|---|---|---|
| Pld | W | D | L | GF | GA | GD | ||
| Pld | W | D | L | GF | GA | GD |
| Team | ||||||||
|---|---|---|---|---|---|---|---|---|
| 3 | 1 | 1 | 1 | 4 | 6 | -2 | ||
| 4 | 1 | 1 | 2 | 3 | 3 | 0 | ||
| Total | 7 | 2 | 2 | 3 | 7 | 9 | -2 |