2002 World Cup qualification

Anguilla entered the World Cup qualifiers for the first time for the 2002 World Cup in South Korea and Japan.

In the first round of the qualifiers, Anguilla were drawn against the Bahamas. On 5 March 2000, Anguilla hosted the first leg in front of 250 people at Webster Park in The Valley, losing by a scoreline of 3–1. In front of a Bahamian crowd of just 330, the second leg was played at the Thomas Robinson Stadium in Nassau on 19 March 2000, with Anguilla losing 2–1, and thereby eliminated by an aggregate scoreline of 5–2.^[4]

2006 World Cup qualification

During the qualifiers for the 2006 World Cup in Germany, Anguilla faced the Dominican Republic in the first round. The first leg was played to a goalless draw at the Estadio Olímpico Juan Pablo Duarte in Santo Domingo on 19 March 2004. Newly introduced FIFA stadium requirements forced Anguilla to play their "home" leg at the same Dominican Republic stadium two days later, with the Dominican Republic winning the second leg and thus the first round by a scoreline of 6–0.

2010 World Cup qualification

During the qualifiers for the 2010 World Cup in South Africa, Anguilla was drawn against El Salvador in the first round. On 6 February 2008, they lost 12–0 at the Estadio Cuscatlán in San Salvador, where striker Rudis Corrales scored five times and Ronald Cerritos three. This time, Anguilla played their "home leg" at RFK Stadium in Washington, D.C. in the United States on 26 March 2008. In front of 22,670 spectators, Anguilla lost the second leg 4–0, thereby losing to El Salvador by an aggregate score of 16–0.

2014 World Cup qualification

In the first round of the qualifiers for the 2014 World Cup in Brazil, Anguilla were again drawn to play the Dominican Republic, as they had eight years previously. On 8 July 2011, they lost 2–0 at the Estadio Panamericano in San Cristobal, and losing 4–0 in the same Dominican Republic stadium just two days later. This put the Dominican Republic through to the second round with the same 6–0 aggregate scoreline as their previous encounter.

2018 World Cup qualification

In the first round of the qualifiers for the 2018 World Cup in Russia, Anguilla were drawn to play Nicaragua. On 23 March 2015, they lost the first leg 5–0 at the Estadio Nacional Dennis Martínez in Managua, Nicaragua and, on 29 March 2015, were eliminated at Ronald Webster Park in The Valley in Anguilla with a 3–0 loss, to send Nicaragua through to the second round by a score of 8–0 on aggregate.

2022 World Cup qualification

In the first round of the qualifiers for the 2022 World Cup in Qatar, Anguilla were drawn into group D with Dominica, Barbados, Dominican Republic, and Panama, whom they’d each play once. Their first match of the campaign was against Dominican Republic on 27 March 2021, at the DRV PNK Stadium in Fort Lauderdale. This game would make it the 3rd time the two teams faced in World Cup qualifying games. Anguilla lost 6–0, making this the same as the last two aggregate scores for the teams. On 31 March 2021, they faced Barbados at Estadio Olímpico Félix Sánchez in Santo Domingo, Anguilla lost to a late 1–0 goal by Emile Saimovici. Then, on 2 June 2021 they lost 3–0 to Dominica at Estadio Olímpico Félix Sánchez in Santo Domingo. And on 6 July, at Estadio Nacional de Panamá in Panama City, Anguilla suffered a massive 13–0 defeat. They ended of round 1 with 0 points, 0 goals, and 23 goals against.

Overall World Cup qualification record

The pair of shutouts against Nicaragua in March 2015 extended Anguilla's scoreless run in World Cup qualification to eight matches, encompassing three World Cups over an eleven-year period. The goals Anguilla scored in March 2000 against the Bahamas in each leg of their first World Cup qualifying appearance remain their only two goals, with 41 goals conceded, no wins, one draw and nine losses from their ten World Cup qualifying matches to date.^[5]

2023

Anguilla  v  Saint Martin

4 March Friendly	Anguilla	2–2	Saint Martin	The Valley, Anguilla
16:00 UTC−4	Hughes 11' Jordan Deans 26'	Report	Cordero 74' Chilin 90+5'	Stadium: Raymond E. Guishard Stadium

Anguilla  v  Saint Lucia

24 March 2022–23 Nations League	Anguilla	1–2	Saint Lucia	The Valley, Anguilla
15:00 UTC−4	Carpenter 76'	Report	Remy 18' President 45+2'	Stadium: Raymond E. Guishard Stadium Referee: Moeth Gaymes (Saint Vincent and the Grenadines)

Anguilla  v  Saint Martin

7 September 2023–24 Nations League	Anguilla	0–6	Saint Martin	The Valley, Anguilla
16:00 UTC−4		Report	Raga 6', 32', 38', 40' Segarel 25' Lacazette 70'	Stadium: Raymond E. Guishard Stadium Referee: Fernando Hernández (Mexico)

Bonaire  v  Anguilla

12 October 2023–24 Nations League	Bonaire	2–0	Anguilla	Rincon, Bonaire
19:00 UTC−4	Ronde 10' Pourier 36'	Report		Stadium: Stadion Antonio Trenidat Attendance: 660 Referee: Norberto da Silva (Curaçao)

Saint Martin  v  Anguilla

16 October 2023–24 Nations League	Saint Martin	8–0	Anguilla	Basseterre, Saint Kitts and Nevis
16:00 UTC−4	Segarel 17', 32' (pen.), 39', 47' Richardson 49' Raga 65', 70', 88'	Report		Stadium: SKNFA Technical Center Referee: Jaime Herrera (El Salvador)

Anguilla  v  Bonaire

18 November 2023–24 Nations League	Anguilla	0–3	Bonaire	The Valley, Anguilla
15:00 UTC−4		Report	Anthony 2', 6' (pen.) Michiel 73'	Stadium: Raymond E. Guishard Stadium Attendance: 267 Referee: Tristley Bassue (Saint Kitts and Nevis)

Current squad

The following players were called up for the CONCACAF Nations League match against Bonaire on 18 November 2023.^[6]

Caps and goals are updated as of 18 November 2023, after the match against Bonaire.

No.	Pos.	Player	Date of birth (age)	Caps	Goals	Club
	1GK	Jelanie Lawrence	(1983-08-26) 26 August 1983	6	0	Doc's United
	1GK	Danniell Bailey	(2003-11-23) 23 November 2003	5	0	Lymers
	1GK	Micah Brooks	(2006-04-30) 30 April 2006	0	0	Diamond
	1GK	Shemor Browne	(2008-07-06) 6 July 2008	0	0
	2DF	Kion Lee	(1993-09-02) 2 September 1993	21	1	Attackers
	2DF	Kieron Lake-Bryan	(2001-10-23) 23 October 2001	8	0
	2DF	Alexander Fleming	(2005-04-12) 12 April 2005	6	0	Diamond
	2DF	Delani Francis	(2006-01-24) 24 January 2006	5	0	Uprising
	2DF	Nicholson Millington	(2008-08-03) 3 August 2008	0	0	Diamond
	3MF	Steven Austin	(1990-12-27) 27 December 1990	12	1	Doc's United
	3MF	Vershawn Hodge	(1994-08-02) 2 August 1994	10	0	Attackers
	3MF	Jermal Richardson	(1994-05-10) 10 May 1994	9	0	Roaring Lions
	3MF	Jalen Smeins	(2002-08-29) 29 August 2002	6	0	Diamond
	3MF	Jared Smeins	(2006-10-26) 26 October 2006	5	0	Diamond
	3MF	Mekhi Connor	(2008-01-14) 14 January 2008	3	0	Roaring Lions
	3MF	Jordan Deans	(1995-10-30) 30 October 1995	3	1
	3MF	Keante Brooks	(2007-02-26) 26 February 2007	2	0	Spartans
	3MF	Dalek Moore	(2006-08-31) 31 August 2006	2	0	Roaring Lions
	3MF	Jaheim Thompson	(2007-10-06) 6 October 2007	1	0	Chesterfield
	4FW	Jonathan Guishard	(1996-07-02) 2 July 1996	27	1	Doc's United
	4FW	Jauron Gayle	(2004-03-04) 4 March 2004	7	1	Uprising
	4FW	Kyle Lake-Bryan	(2001-10-23) 23 October 2001	6	1	Spartans Youth
	4FW	Defari Francis	(2005-03-11) 11 March 2005	2	0	Uprising

Recent call-ups

The following players have also been called up for the team in the last twelve months.

Most appearances

Top goalscorers

FIFA World Cup

Year	Final Tournament								Qualification
	Round	Pld	W	D	L	GF	GA		Pos.	Pld	W	D	L	GF	GA
1930 to 1998	Not a FIFA member								Not a FIFA member
2002	Did not qualify								First round	2	0	0	2	2	5
2006									First round	2	0	1	1	0	6
2010									First round	2	0	0	2	0	16
2014									First round	2	0	0	2	0	6
2018									First round	2	0	0	2	0	8
2022									First round – 4th	4	0	0	4	0	23
2026	To be determined								To be determined
2030
2034
Totals	0/6	–	–	–	–	–	–		—	14	0	1	13	2	64

Draws include knockout matches decided on penalty kicks; correct as of 5 June 2021 after the match against Panama.

CONCACAF Gold Cup

Year	Final Tournament								Qualification
	Round	Pld	W	D	L	GF	GA		Pos.	Pld	W	D	L	GF	GA
1963 to 1989	Not a CONCACAF member								Not a CONCACAF member
1991	Did not qualify								3rd	2	0	1	1	1	7
1993									3rd	2	0	0	2	0	2
1996									First round	2	0	0	2	2	6
1998									4th	3	0	0	3	1	12
2000									4th	3	0	0	3	1	35
2002									2nd	2	1	0	1	5	4
2003	Did not enter								Did not enter
2005	Withdrew								Withdrew
2007	Did not qualify								4th	3	0	0	3	5	18
2009									3rd	2	0	0	2	2	6
2011									3rd	3	1	0	2	4	8
2013									4th	3	0	0	3	1	16
2015									4th	3	0	0	3	0	20
2017									3rd	2	0	0	2	0	11
2019									31st	4	0	1	3	1	15
2021									3rd	4	0	0	4	2	21
2023									2nd	4	0	2	2	2	5
Totals	0/17	–	–	–	–	–	–		—	42	2	4	36	27	186

Draws include knockout matches decided via penalty shoot-out; correct as of 23 March 2023 after the match against Saint Lucia.

CONCACAF Nations League

CONCACAF Nations League record
Season	Division	Group	Pld	W	D	L	GF	GA	P/R	Rank
2019−20	C	C	4	0	0	4	2	21		41st
2022–23	C	C	4	0	2	2	2	5		37th
2023–24	C	A	4	0	0	4	0	19		39th
Total			12	0	2	10	4	45	37th

Draws include knockout matches decided via penalty shoot-out; correct as of 18 November 2023 after the match against Bonaire.

Caribbean Cup

Year	Final Tournament								Qualification
	Round	Pld	W	D	L	GF	GA		Pos.	Pld	W	D	L	GF	GA
1989 to 1990	Did not enter								Did not enter
1991	Did not qualify								3rd	2	0	1	1	1	7
1992									First round	2	0	0	2	0	8
1993									3rd	2	0	0	2	0	2
1994									3rd	2	0	0	2	0	11
1995									First round	2	0	0	2	2	6
1996									3rd	2	0	0	2	0	12
1997									4th	3	0	0	3	1	12
1998									4th	3	0	0	3	1	35
1999	Withdrew								Withdrew
2001	Did not qualify								2nd	2	1	0	1	5	4
2005	Withdrew								Withdrew
2007	Did not qualify								4th	3	0	0	3	5	18
2008									3rd	2	0	0	2	2	6
2010									3rd	3	1	0	2	4	8
2012									4th	3	0	0	3	1	16
2014									4th	3	0	0	3	0	20
2017									3rd	2	0	0	2	0	11
Totals	0/19	–	–	–	–	–	–		—	36	2	1	33	21	176