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Country Radio Top 20 | |||
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9/3/1999 | |||
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| 1 | 3 | Single White Female Chely Wright | 13 |
| 2 | 4 | You Had Me From Hello Kenny Chesney | 10 |
| 3 | 1 | Amazed Lonestar | 15 |
| 4 | 2 | Lesson In Leavin' Jo Dee Messina | 15 |
| 5 | 6 | The Secret Of Life Faith Hill | 11 |
| 6 | 9 | Something Like That Tim McGraw | 5 |
| 7 | 7 | Little Man Alan Jackson | 10 |
| 8 | 10 | Ready To Run Dixie Chicks | 7 |
| 9 | 5 | (God Must Have Spent) A Little More Time On You Alabama | 16 |
| 10 | 13 | I Love You Martina McBride | 4 |
| 11 | 8 | Little Good-Byes SheDaisy | 14 |
| 12 | 12 | I'll Still Love You More Trisha Yearwood | 7 |
| 13 | 11 | Write This Down George Strait | 20 |
| 14 | 15 | (Now You See Me) Now You Don't Lee Ann Womack | 6 |
| 15 | 19 | What Do You Say To That George Strait | 2 |
| 16 | 20 | She's In Love Mark Wills | 3 |
| 17 | - | I'm Already Taken Steve Wariner | 1 |
| 18 | 14 | A Night To Remember Joe Diffie | 15 |
| 19 | 18 | This Heartache Never Sleeps Mark Chesnutt | 7 |
| 20 | - | Lonely And Gone Montgomery Gentry | 1 |