Anguilla

Months as Worst in the World :	66
When? :	May 1997 – May 1997 (1 month) February 1998 – February 1998 (1 month) July 1998 – July 1998 (1 month) November 1998 – November 1998 (1 month) January 1999 – February 1999 (2 months) November 1999 – February 2000 (4 months) July 2006 – July 2006 (1 month) April 2008 – May 2011 (37 months) April 2015 – present (18 months)
All-Time Worst in the World Ranking :	4th
Anguilla on FIFA
Anguilla on CONCACAF

Anguilla Article Links
Caribbean Cup Qualifier: Guyana 7-0 Anguilla	World Rankings: Anguilla’s Points Expunged	Richard Orlowski – Man on a Mission
Welcome Back Anguilla	Bhutan hit the heights, Anguilla fall	Anguilla outgunned by Nicaragua to seal fall to Worst in the World

Matches played as Worst in the World
25th February 2000	Friendly		British Virgin Islands 3-4 Anguilla
27th February 2000	Friendly		British Virgin Islands 4-0 Anguilla
5th March 2000	World Cup Qualifier		Anguilla 1-3 Bahamas
17th September 2008	Caribbean Cup		St Vincent & the Grenadines 3-1 Anguilla
18th September 2010	Caribbean Championship		British Virgin Islands 2-1 Anguilla
2nd October 2010	Caribbean Championship		Puerto Rico 3-1 Anguilla
4th October 2010	Caribbean Championship		Cayman Islands 4-1 Anguilla
19th June 2011	Friendly		Anguilla 0-0 British Virgin Islands
23rd March 2016	Caribbean Cup Qualifier		Guyana 7-0 Anguilla		Report