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Country Radio Top 20 | |||
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10/15/1999 | |||
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| 1 | 1 | Something Like That Tim McGraw | 11 |
| 2 | 2 | I Love You Martina McBride | 10 |
| 3 | 3 | Ready To Run Dixie Chicks | 13 |
| 4 | 4 | I'm Already Taken Steve Wariner | 7 |
| 5 | 5 | What Do You Say To That George Strait | 8 |
| 6 | 9 | Lonely And Gone Montgomery Gentry | 7 |
| 7 | 13 | She's In Love Mark Wills | 9 |
| 8 | 12 | Home To You John Michael Montgomery | 5 |
| 9 | 7 | Amazed Lonestar | 21 |
| 10 | 10 | Lesson In Leavin' Jo Dee Messina | 21 |
| 11 | 14 | I'll Go Crazy Andy Griggs | 6 |
| 12 | 15 | When I Said I Do Clint Black w/ Lisa Hartman-Black | 3 |
| 13 | 6 | You Had Me From Hello Kenny Chesney | 16 |
| 14 | 8 | Little Man Alan Jackson | 16 |
| 15 | 16 | Missing You Brooks & Dunn | 4 |
| 16 | 11 | I'll Still Love You More Trisha Yearwood | 13 |
| 17 | 18 | Come On Over Shania Twain | 2 |
| 18 | 20 | He Didn't Have To Be Brad Paisley | 2 |
| 19 | - | All Things Considered Yankee Grey | 1 |
| 20 | 19 | Lightning Does The Work Chad Brock | 2 |