| 100 (-344 to -329) Cayman Islands 1(0) - 1(1) Cuba (-240 to -247) 50: 31MAY2019 |
| 100 (-422 to -344) Cayman Islands 1(0) - 0(0) Cuba (-201 to -240) 50: 29MAY2019 |
| 100 (-414 to -422) Cayman Islands 1(1) - 3.5(2) Montserrat (17 to 29) 150: 22MAR2019 |
| 90 (-448 to -414) Cayman Islands 0(0) - 0(0) Saint Lucia (-107 to -145) 100: 17NOV2018 |
| 80 (-180 to -165) Dominicana 3(3) - 1(0) Cayman Islands (-431 to -448) 90: 12OCT2018 |
| 75 (-314 to -283) Cuba 5(5) - 1(0) Cayman Islands (-375 to -431) 135: 29SEP2018 |
| 75 (33 to 40) Jamaica 4(4) - 0.5(0) Cayman Islands (-362 to -375) 135: 09SEP2018 |
| 120 (-393 to -362) Cayman Islands 1(1) - 1(1) Belize (-194 to -212) 70: 29MAR2015 |
| 70 (-172 to -194) Belize 0(0) - 0(0) Cayman Islands (-431 to -393) 120: 25MAR2015 |
| 70 (-484 to -431) Cayman Islands 2(1) - 1(1) Dominicana (-289 to -333) 58: 14NOV2011 |
| 87 (-317 to -289) Dominicana 4(4) - 1(0) Cayman Islands (-451 to -484) 105: 11NOV2011 |
| 38 (-27 to -24) Salvador 4(4) - 1(0) Cayman Islands (-442 to -451) 105: 11OCT2011 |
| 70 (-437 to -442) Cayman Islands 0.5(0) - 1(1) Suriname (5 to 10) 70: 07OCT2011 |
| 70 (-431 to -437) Cayman Islands 2(1) - 4(4) Salvador (-32 to -30) 25: 06SEP2011 |
| 70 (-9 to -3) Suriname 1(1) - 0.5(0) Cayman Islands (-425 to -431) 70: 02SEP2011 |
| 70 (-492 to -444) Puerto Rico 2(2) - 1(0) Cayman Islands (-356 to -425) 100: 06OCT2010 |
| 100 (-403 to -356) Cayman Islands 4(4) - 2(1) Anguilla (-427 to -474) 100: 04OCT2010 |
| 100 (-361 to -403) Cayman Islands 1(1) - 1.5(1) French Saint Martin (-306 to -268) 90: 02OCT2010 |
| 25 (-119 to -114) Grenada 4.5(4) - 2(2) Cayman Islands (-349 to -361) 58: 15OCT2008 |
| 58 (-341 to -349) Cayman Islands 0(0) - 1(1) Martinique (-17 to -9) 58: 13OCT2008 |
| 75 (37 to 45) Guadeloupe 'C' 7(7) - 1(1) Cayman Islands (-332 to -341) 87: 11OCT2008 |
| 58 (-345 to -332) Cayman Islands 0(0) - 0(0) Bermuda (-175 to -190) 64: 31AUG2008 |
| 58 (-322 to -345) Cayman Islands 1(1) - 1.5(1) Antigua Barbuda (-251 to -241) 25: 30AUG2008 |
| 58 (-362 to -322) Cayman Islands 3(3) - 0.5(0) French Saint Martin (-227 to -296) 100: 27AUG2008 |
| 58 (-345 to -362) Cayman Islands 1(1) - 3(3) Bermuda (-198 to -179) 64: 30MAR2008 |
| 64 (-183 to -198) Bermuda 1(1) - 1(1) Cayman Islands (-358 to -345) 58: 03FEB2008 |
| 105 (62 to 71) Cuba 7(7) - 1(0) Cayman Islands (-345 to -358) 150: 06SEP2006 |
| 100 (-305 to -345) Cayman Islands 0(0) - 2.5(2) Turks Caicos Islands (-231 to -191) 100: 04SEP2006 |
| 70 (-323 to -280) Bahamas 3(3) - 1.5(1) Cayman Islands (-244 to -305) 100: 02SEP2006 |
| 38 (58 to 64) Saint Vincent Grenadines 4.5(4) - 0(0) Cayman Islands (-224 to -244) 120: 28NOV2004 |
| 64 (-345 to -369) British Virgin Islands 0.5(0) - 1(1) Cayman Islands (-254 to -224) 80: 26NOV2004 |
| 64 (-72 to -54) Bermuda 2(2) - 1(1) Cayman Islands (-231 to -254) 80: 24NOV2004 |
| 70 (14 to 29) Cuba 3(3) - 1(0) Cayman Islands (-214 to -231) 80: 27MAR2004 |
| 80 (-241 to -214) Cayman Islands 2(1) - 2(2) Cuba (37 to 14) 70: 22FEB2004 |
| 150 (-217 to -241) Cayman Islands 0(0) - 3(3) Martinique (69 to 86) 105: 01DEC2002 |
| 80 (-210 to -258) Dominicana 0(0) - 2(1) Cayman Islands (-277 to -217) 100: 29NOV2002 |
| 150 (-240 to -277) Cayman Islands 1(0) - 5(5) Cuba (-46 to -16) 120: 27NOV2002 |
| 58 (71 to 49) Martinique 1(1) - 1(1) Cayman Islands (-278 to -240) 100: 08APR2001 |
| 100 (-28 to -7) Saint Vincent Grenadines 1.5(1) - 1(1) Cayman Islands (-257 to -278) 100: 06APR2001 |
| 100 (-186 to -257) Cayman Islands 2(2) - 2.5(2) British Virgin Islands (-343 to -286) 80: 04APR2001 |
| 120 (-278 to -186) Cayman Islands 1(0) - 0(0) Cuba (-70 to -115) 58: 19MAR2000 |
| 87 (-99 to -70) Cuba 4(4) - 1(0) Cayman Islands (-218 to -278) 180: 05MAR2000 |
| 80 (-258 to -218) Cayman Islands 2(2) - 0(0) Netherlands Antilles (-260 to -295) 70: 26JUL1998 |
| 64 (-15 to -1) Haiti 1(1) - 0.5(0) Cayman Islands (-241 to -258) 80: 24JUL1998 |
| 38 (160 to 164) Jamaica 4(4) - 0.5(0) Cayman Islands (-229 to -241) 120: 22JUL1998 |
| 80 (-283 to -229) Cayman Islands 2(2) - 0(0) Bermuda (-155 to -236) 120: 10MAY1998 |
| 80 (-346 to -283) Cayman Islands 3(2) - 2(2) Cuba (-113 to -184) 90: 06MAY1998 |
| 38 (-66 to -59) Cuba 5(5) - 1(0) Cayman Islands (-317 to -346) 150: 13MAY1996 |
| 100 (-352 to -317) Cayman Islands 1(0) - 1(1) Cuba (-57 to -66) 25: 11MAY1996 |
| 150 (-325 to -352) Cayman Islands 1(0) - 4(4) Cuba (-64 to -57) 38: 26APR1996 |
| 90 (-306 to -325) Cayman Islands 1(0) - 3(3) Cuba (-76 to -64) 58: 30JUL1995 |
| 135 (-289 to -306) Cayman Islands 2.5(2) - 9(9) Trinidad Tobago (43 to 54) 87: 28JUL1995 |
| 90 (-283 to -289) Cayman Islands 2(2) - 2.5(2) Saint Vincent Grenadines (181 to 185) 58: 25JUL1995 |
| 90 (-359 to -283) Cayman Islands 2(2) - 0.5(0) Antigua Barbuda (-59 to -127) 80: 21JUL1995 |
| 105 (-427 to -350) Puerto Rico 4(4) - 1(0) Cayman Islands (-248 to -359) 150: 14MAR1993 |
| 150 (-127 to -65) Barbados 6(6) - 1.5(1) Cayman Islands (-186 to -248) 150: 12MAR1993 |
| 100 (-102 to -58) Guyana 3.5(3) - 2(2) Cayman Islands (-142 to -186) 100: 11MAR1993 |