| THABO | President of South Africa from 1999 to 2008 (5,5) |
| MBEKI | President of South Africa from 1999 to 2008 (5,5) |
| HELEN | Prime Minister of New Zealand from 1999 to 2008 (5,5) |
| CLARK | Prime Minister of New Zealand from 1999 to 2008 (5,5) |
| WARNERBROS | Barry Meyer, who got his J.D. at CWRU, was CEO of this entertainment company from 1999 to 2013 |
| STEVEWAUGH | Australian cricket captain from 1999 to 2004 (5,5) |
| JACKDORSEY | He was Twitter's CEO from 2006 to 2008, and then again from 2015 to 2020 |
| SUPERNANNY | British reality TV show starring Jo Frost, which ran from 2004 to 2008 (10) |
| MENINTREES | 2006 to 2008 ABC drama with Anne |
| OBASANJO | Olusegun ___, military ruler of Nigeria from 1976 to 1979 and president from 1999 to 2007 (8) |
| SCI | ___ Fi (name of a cable network from 1999 to 2009) |
| EHUDBARAK | Prime minister of Israel from 1999 to 2001 (4,5) |
| WAUGH | Steve ___, captain of the Australian Test cricket team from 1999 to 2004 |
| ROBERTSON | George --, Secretary General of NATO from 1999 to 2004 (9) |
| HUSSAIN | Captain of the England Test cricket team from 1999 to 2003 (6,7) |
| BARAK | Deborah's assistant - PM of Israel from 1999 to 2001 (5) |
| ADRIENNE | Ms. Clarkson (Governor General of Canada, from 1999 to 2005) |
| ALANMILBURN | Labour Secretary of State for Health from 1999 to 2003 (4,7) |
| ADRIENNECLARKSON | Governor General of Canada from 1999 to 2005 also famously a journalist: 2 wds. |
| NASSERHUSSAIN | Captain of the England cricket team for 45 Test matches from 1999 to 2003 |
