1985–2000

The Caymanian football team played its first international match on 3 March 1985, against Dominica, in Roseau, as part of the 1985 CFU Championship. They lost that match 2–1 with Lee Ramoon - who would go on to become the team's top scorer - opening the scoring.

They qualified for the 1991 Caribbean Cup, falling in the first round. They returned to the tournament in 1994, suffering the same fate. However, the following year, the Cayman Islands jointly organized with Jamaica the 1995 Caribbean Cup, reaching the semi-finals. It fell to Trinidad and Tobago by a scandalous 2–9, the worst defeat in its history. In the match for 3rd place, they were defeated by Cuba 0–3. They would qualify again in 1998 although they failed to get past the group stage. They have not played a Caribbean Cup final phase since then.

The Cayman Islands participated in their first World Cup qualifying tie in the 1998 where they succumbed in the first round at the hands of Cuba, who eliminated them after winning twice 0–1 and 0–5.

2000–2010

In 2000, given the status of the Cayman Islands as one of the British overseas territories, the national team attempted to use this as a loophole to call up a number of uncapped players possessing British passports but who had no specific links to the islands. Barry McIntosh, a football agent, was called in to scout players for an upcoming FIFA World Cup qualifier against Cuba and ultimately he secured eight players i.e. Wayne Allison (Tranmere Rovers), Ged Brannan (Motherwell), David Barnett (Lincoln City), Martin O'Connor (Birmingham City), Dwayne Plummer (Bristol City), Barry Hayles (Fulham), Neville Roach (Southend United) and Neil Sharpe (Boreham Wood). With the exception of Allison the players all appeared in a 5–0 friendly defeat against D.C. United but before they could appear in any official internationals FIFA stepped in and barred the players from representing the Cayman Islands due to their failure to satisfy the existing rules for national team eligibility.^[2] Of the eight players only Hayles went on to play international football, appearing for Jamaica ten times.

In the first round of the 2002 qualifiers, Cayman Islands was once again eliminated by Cuba, winning 4–0 in Havana and drawing 0–0 in George Town. History repeated itself four years later, in the 2006 qualifiers, since the Cubans eliminated the Caymanian team from the World Cup for the third time in a row (1–2 in George Town and 4–0 in Havana).

Things didn't change significantly for the 2010 qualifiers, only this time it was Bermuda that eliminated the Cayman Islands in the first round, 4–2 on aggregate. Regardless, this tie saw the Caymanians earn their first points away from home, earning a 1–1 draw at Hamilton on 3 February 2008, with Allean Grant scoring in the 87th minute.

2010–present

Qualifying directly into the second round of the 2014 qualifiers, the Cayman Islands were drawn in group A along with their peers from El Salvador, the Dominican Republic and Suriname. They lost 5 games out of 6, rescuing a 1-1 draw on the last day, on 14 November 2011, against the Dominicans. The Caymanian team did not play any match again in the next few years, since declining their participation in the 2012 and 2014 Caribbean Cups. But they returned to the 2018 qualifiers, facing Belize in the first round. The first leg in Belmopan finished 0–0 and the second leg in George Town finished 1–1. The 1–1 aggregate score meant the Cayman Islands were eliminated on the away goal rule. With this unbeaten elimination, Cayman Islands can say that they are one of the few teams in the world that did not qualify for a FIFA World Cup despite not losing a single match.

2023

Puerto Rico  v  Cayman Islands

26 March 2022–23 Nations League	Puerto Rico	5–1	Cayman Islands	Bayamón, Puerto Rico
18:00 UTC−4	Rivera 2', 70' Díaz 40' Burgos 89', 90+2'	Report	Studenhofft 85'	Stadium: Estadio Juan Ramón Loubriel Referee: Ekaterina Koroleva (United States)

U.S. Virgin Islands  v  Cayman Islands

7 September 2023–24 Nations League	U.S. Virgin Islands	2–2	Cayman Islands	Saint Croix, U.S. Virgin Islands
19:00 UTC−4	McLaughlin 23' (o.g.) St. Louis 42'	Report	Jo. Ebanks 16' Gray 47'	Stadium: Bethlehem Soccer Stadium Referee: Reon Radix (Grenada)

Cayman Islands  v  Aruba

11 September 2023–24 Nations League	Cayman Islands	1–2	Aruba	George Town, Cayman Islands
15:30 UTC−5	Reeves 6'	Report	Ostiana 2' Bäly 79'	Stadium: Truman Bodden Sports Complex Referee: Ismael Cornejo (El Salvador)

Cayman Islands  v  U.S. Virgin Islands

17 October 2023–24 Nations League	Cayman Islands	2–1	U.S. Virgin Islands	George Town, Cayman Islands
15:30 UTC−5	Seymour 17' Reeves 57'	Report	Joseph 84'	Stadium: Truman Bodden Sports Complex Referee: Randy Encarnación (Dominican Republic)

Aruba  v  Cayman Islands

20 November 2023–24 Nations League	Aruba	5–1	Cayman Islands	Oranjestad, Aruba
15:00 UTC−4	Groothusen 16', 89' Ostiana 45+5' Maria 55' Dania 77'	Report	Studenhofft 49'	Stadium: Trinidad Stadium Referee: Norberto da Silva (Curaçao)

Current squad

• The following players were called up for Nations League.^[3]
• Match dates: 26 March 2023
• Opposition:  Puerto Rico
• Caps and goals correct as of: 26 March 2023, after the match against  Puerto Rico

No.	Pos.	Player	Date of birth (age)	Caps	Goals	Club
1	1GK	Johnathan Mclean-Giraud	(1997-12-11) 11 December 1997	1	0	East End United
	1GK	Devante Whittaker	(2005-01-20) 20 January 2005	0	0
	2DF	Joshewa Frederick-Charlery	(1997-01-24) 24 January 1997	19	0	Tunari
	2DF	D'Andre Rowe	(2001-01-05) 5 January 2001	10	0	Scholars International
	2DF	Trey Ebanks	(2000-06-05) 5 June 2000	8	0	Academy
	2DF	Jah Dain Alexander	(1999-12-08) 8 December 1999	1	0	Elite
	2DF	Andray Reynolds	(2000-11-28) 28 November 2000	1	0
	3MF	Barry-Dre Tibbetts	(2002-06-05) 5 June 2002	6	0	Dakota Wesleyan University
	3MF	Shakurn Silburn	(1999-08-12) 12 August 1999	2	0	Elite
	3MF	Jordan Bonilla	(1997-02-28) 28 February 1997	1	0	Scholars International
	3MF	Casey Mclaughlin	(1996-04-28) 28 April 1996	1	0	Bodden Town
	3MF	Francisco Murillo	(1999-08-26) 26 August 1999	1	0
	4FW	Mark Ebanks	(1990-12-26) 26 December 1990	23	7	Academy
	4FW	Mason Duval	(2001-08-24) 24 August 2001	8	0	Elon University
	4FW	Martin Webb	(1995-09-07) 7 September 1995	7	0	Cayman Athletic
	4FW	Elijah Seymour	(1998-11-05) 5 November 1998	5	0	Electric City
	4FW	Anthony Nelson	(1997-07-31) 31 July 1997	4	0	Sunset
	4FW	Gunnar Studenhofft	(2002-04-05) 5 April 2002	2	1	Manhattan College
	4FW	Kailan Miller	(2000-10-07) 7 October 2000	0	0
	4FW	Jacobbi Tugman	(2004-10-03) 3 October 2004	0	0	CSM Alexandria

Recent call-ups

Most appearances

Top goalscorers

FIFA World Cup

FIFA World Cup record										FIFA World Cup qualification record
Year	Round	Position	Pld	W	D*	L	GF	GA		Pld	W	D	L	GF	GA
1930 to 1994	Not a FIFA member									Not a FIFA member
1998	Did not qualify									2	0	0	2	0	6
2002										2	0	1	1	0	4
2006										2	0	0	2	1	5
2010										2	0	1	1	2	4
2014										6	0	1	5	2	15
2018										2	0	2	0	1	1
2022										4	0	1	3	2	18
2026	To be determined									To be determined
2030
2034
Total	–	0/7	–	–	–	–	–	–		20	0	6	14	8	53

CONCACAF Gold Cup

CONCACAF Gold Cup record
Year	Round	Position	Pld	W	D*	L	GF	GA
1991	Did not qualify
1993
1996
1998	Withdrew
2000	Did not qualify
2002
2003
2005
2007
2009
2011
2013	Withdrew
2015
2017
2019	Did not qualify
2021
2023
Total	–	0/17	–	–	–	–	–	–

CONCACAF Nations League

CONCACAF Nations League record
Season	Division	Group	Pld	W	D*	L	GF	GA	P/R	Rank
2019−20	C	A	6	4	0	2	7	8		33rd
2022–23	C	D	4	0	2	2	3	11		40th
2023–24	C	B	4	1	1	2	6	10		37th
Total			14	5	3	6	16	29	33rd

Caribbean Cup

Caribbean Cup record
Year	Round	Pld	W	D[decimal 1]	L	GF	GA
1989	Did not enter
1990	Did not qualify
1991	Group stage	2	0	0	2	3	5
1992	Did not qualify
1993
1994	Group stage	3	0	1	2	3	6
1995	Fourth place	5	2	1	2	7	14
1996	Did not qualify
1997	Withdrew
1998	Group stage	3	1	0	2	2	5
1999	Did not qualify
2001
2005
2007
2008
2010
2012	Did not enter
2014
2017
Total	4/19	13	3	2	8	15	30