| 100% | INDYTIMESFOUR | 13 | 2000 = the miles of ___ |
| 70% | POUNDSINATON | 12 | 2000 = the number of ___ |
| 70% | STATESTIMESFORTY | 16 | 2000 = the number of ___ |
| 69% | ASIA | 4 | 17+ million square miles of the earth |
| 68% | SYR | 3 | Setting for 400+ miles of the Euphrates: Abbr. |
| 67% | YUKON | 5 | Home to nearly 600 miles of the Alaska Highway |
| 66% | NONET | 5 | Miles Davis ___ (“Birth of the Cool” ensemble) |
| 66% | NONET | 5 | Miles Davis ___ ("Birth of the Cool" ensemble) |
| 66% | SQUARESINTHIS | 13 | 2000 = the number of ___ (with 92 Across) |
| 66% | NAUTICAL | 8 | __ Mile, distance measurement of the sea |
| 66% | EDINBURGH | 9 | Home of the royal mile |
| 66% | SYDNEY | 6 | Host of the 2000 Olympics |
| 66% | SYDNEY | 6 | Site of the 2000 Olympics |
| 65% | TWENTYSIX | 9 | The number of complete miles in a marathon |
| 65% | DAVIS | 5 | "Birth of the Cool" trumpeter Miles |
| 64% | MYA | 3 | "Case of the Ex" singer, 2000 |
| 64% | STLOUISRAMS | 11 | Winners of the 2000 Super Bowl |
| 64% | NONETS | 6 | Miles's "Birth of the Cool" group, and others |
| 64% | NANTUCKET | 9 | The island located 30 miles south of Cape Cod |
| 63% | ADEN | 4 | Site of the 2000 USS Cole attack |
| 63% | VIJAY | 5 | Golfer Singh, winner of the 2000 Masters |
| 63% | SYD | 3 | Aptly named mascot of the 2000 Olympics |
| 63% | AUS | 3 | Home of the 2000 Summer Olympics: Abbr. |
| 63% | NONETS | 6 | Miles Davis’s “Birth of the Cool” group, and others |
| 62% | MALTA | 5 | Smallest member of the eurozone (122 square miles) |
| 62% | SPOKANE | 7 | City 18 miles west of the Idaho border |
| 62% | CLOSEVOTE | 9 | Feature of the 1876 or 2000 presidential election |
| 62% | AALIYAH | 7 | Singer of the #1 single "Try Again," 2000 |
| 62% | BRADPITT | 8 | Male half of the 2000's couple Brangelina |
| 62% | ESA | 3 | Group in charge of the Horizon 2000 program |