| WILKINSON | Howard ......... , England football caretaker manager in 1999 and 2000 (9) |
| MARTINEZ | Pitcher Pedro who won the NL Cy Young Award in 1997, and the AL Cy Young Award in 1999 and 2000 |
| HODDLE | Who was sacked as England manager in 1999 after making controversial comments about the disabled? (6) |
| LANCE | Cyclist Armstrong who won the Tour de France in 1999 and 2000 |
| MUSHARRAF | Military officer who took power in Pakistan in a coup (1999) and who later served as president (2001-08) |
| GREENAWAY | Peter ___, British director of films including 8.5 Women (1999) and Walking to Paris (2021) (9) |
| TOMRIPLEY | Sociopathic role for Alain Delon (1960), Matt Damon (1999) and John Malkovich (2002) |
| TORRE | Winning World Series manager in 1996, 1998, 1999 and 2000 |
| PAGE | Robert, Wales' football team caretaker manager in Euro 2020 (4) |
| NEVAEH | Anagrammatic girls' name given to eight babies in 1999, and 4,457 in 2005 |
| PAYBACK | Crime thriller released in 1999 and starring Mel Gibson and Lucy Liu (7) |
| ISTABRAQ | Champion Hurdle winner in 1998, 1999 and 2000 (8) |
| YANKEES | World Series champs in 1998, 1999, and 2000 (7) |
| ROTAN | 2013-18 Ukraine midfielder; their caretaker manager in 2023 (5) |
| RUSLAN | 2013-18 Ukraine midfielder; their caretaker manager in 2023 (6) |
| NUNAVUT | Largest and newest territory of Canada, created in 1999 and governed solely by Inuit (7) |
| RONNIEBAXTER | English darts player who was runner-up in the 1999 and 2000 BDO world championships |
| PETESAMPRAS | Men's singles champion at Wimbledon in 1993, 1994, 1995, 1997, 1998, 1999 and 2000 |
| SAMPRAS | Pete ___, men's singles champion at Wimbledon in 1993, 1994, 1995, 1997, 1998, 1999 and 2000 |
| INKSTER | Juli who won the U.S. Women's Open in 1999 and 2002 |
