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September 2018
09 Sept
CONCACAF Nations League Qualification
Jamaica
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4
Cayman Islands
CYM
0
FT
October 2018
12 Oct
CONCACAF Nations League Qualification
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3
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0
FT
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17 Nov
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0
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0
FT
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March 2019
22 Mar
CONCACAF Nations League Qualification
Cayman Islands
CYM
1
Montserrat
MSR
2
FT
June 2024
08 Jun
World Cup Qualification CONCACAF
Cayman Islands
CYM
1
Antigua and Barbuda
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0
FT
11 Jun
World Cup Qualification CONCACAF
Cuba
CUB
3
Cayman Islands
CYM
0
FT
September 2024
04 Sept
CONCACAF Nations League
British Virgin Islands
VGB
0
Cayman Islands
CYM
1
FT
07 Sept
CONCACAF Nations League
Cayman Islands
CYM
1
St. Kitts and Nevis
KNA
4
FT
October 2024
12 Oct
CONCACAF Nations League
Cayman Islands
CYM
1
British Virgin Islands
VGB
0
FT
15 Oct
CONCACAF Nations League
St. Kitts and Nevis
KNA
1
Cayman Islands
CYM
1
FT
November 2024
15 Nov
CONCACAF Nations League
Cayman Islands
CYM
0
Guadeloupe
GOU
6
FT
19 Nov
CONCACAF Nations League
Guadeloupe
GOU
1
Cayman Islands
CYM
0
FT
agg 7 - 0
June 2025
04 Jun
World Cup Qualification CONCACAF
Bermuda
BMU
5
Cayman Islands
CYM
0
FT
07 Jun
World Cup Qualification CONCACAF
Cayman Islands
CYM
0
Honduras
HON
1
FT
March 2026
26 Mar
Friendlies
Cayman Islands
CYM
1
British Virgin Islands
VGB
1
FT
29 Mar
Friendlies
Cayman Islands
CYM
1
Bahamas
BHS
0
FT
June 2026
06 Jun
Friendlies
Gibraltar
GIB
4
Cayman Islands
CYM
1
FT
Cayman Islands
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