| ZULUAGA | Fabiola -, winner in 1999 and from 2002-04 of the Copa Colsanitas singles tennis tournament |
| GETAFE | Spanish city in the south of the Madrid metropolitan area whose football team reached the final of the Copa del Rey in 2007 and 2008 |
| JAMES | Who won the best player of the tournament award in the Copa America 2024? (5) |
| BRASIL | Five-time winner of the Copa do Mundo |
| URUGUAY | Which country scored the most number of goals at the end of the round stages of Copa America 2024, besides finishing third in the tournament? (7) |
| MARTINEZ | Pitcher Pedro who won the NL Cy Young Award in 1997, and the AL Cy Young Award in 1999 and 2000 |
| REALBETIS | Seville-based Spanish football club who won the Copa del Rey in 1977 and 2005 |
| JENNIFERLOPEZ | Let's Get Loud singer who was named Glamour Woman of the Year in 1999 and 2011: 2 wds. |
| INKSTER | Juli who won the U.S. Women's Open in 1999 and 2002 |
| NUNAVUT | Largest and newest territory of Canada, created in 1999 and governed solely by Inuit (7) |
| SCOTLAND | Last winners, in 1999, of the Five Nations Championship; 2004, 2007, 2012 and 2015 Six Nations wooden spoon recipients (8) |
| NEVAEH | Anagrammatic girls' name given to eight babies in 1999, and 4,457 in 2005 |
| LANCE | Cyclist Armstrong who won the Tour de France in 1999 and 2000 |
| PAYBACK | Crime thriller released in 1999 and starring Mel Gibson and Lucy Liu (7) |
| EDITH | Women's short race gold medallist at the World Cross Country Championships from 2002-04 (5,5) |
| EDITHMASAI | Women's short race gold medallist at the World Cross Country Championships from 2002-04 (5,5) |
| JOSE | Who scored the winner for Panama in its win over the host USA in Copa America 2024? (4) |
| NEO | Hero of three science fiction movies in 1999 and 2003 |
| CROUPIER | Film released in 1999 and starring Clive Owen as a casino worker (8) |
| MASAI | Edith ?, World Cross Country Championships short race gold medallist from 2002-04 (5) |
