| HOON | Geoff ___, defence secretary from 1999 to 2005 (4) |
| NOTT | Sir John ___, Defence secretary during the Falklands War (4) |
| DAWSON | R&A secretary from 1999 to 2015 (6) |
| FALLON | Michael, Conservative politician who served as defence secretary from 2014 to 2017 (6) |
| MAPLES | John ___, Shadow Foreign Secretary from 1999-00 (6) |
| WING | Word that follows The West to give the title of a US drama series which ran from 1999 to 2006 (4) |
| WEST | Political saga that aired from 1999 to 2006, The ---- Wing (4) |
| CLARKSON | Adrienne ___ (Canada's 26th Governor General, from 1999 to 2005) |
| ADRIENNE | Ms. Clarkson (Governor General of Canada, from 1999 to 2005) |
| ADRIENNECLARKSON | Governor General of Canada from 1999 to 2005 also famously a journalist: 2 wds. |
| TIMHENMAN | Retired British tennis star ranked British No 1 in 1996 and again from 1999 to 2005 (3,6) |
| EDIE | She played James's husband from 1999 to 2007 |
| HUNT | Geoff ___, 1979 and 1980 World Open squash champion (4) |
| THEE | Megan ___ Stallion, second solo female rapper, after Lauryn Hill in 1999, to win the Grammy for Best New Artist (March, 2021) |
| ALANMILBURN | Labour Secretary of State for Health from 1999 to 2003 (4,7) |
| OBASANJO | Olusegun ___, military ruler of Nigeria from 1976 to 1979 and president from 1999 to 2007 (8) |
| EHUDBARAK | Israeli prime minister from 1999 to 2001 (4,5) |
| ROBERTSON | George --, Secretary General of NATO from 1999 to 2004 (9) |
| ALEROS | Models sold from 1999 to 2004 |
| SCI | ___ Fi (name of a cable network from 1999 to 2009) |
