| Cover | | Date  | Title • Artist  Album | Points  | Charts Peaks | Comment |
|---|
 | 1. | 11/1999 | | 288
 | US 2 UK 33 US AC ✫1 US country ✫1 | [Warner 16884] written by Stephanie Bentley & Holly Lamar |
 | 2. | 01/1999 | | 238
 | US 7 UK 3 US AC 8 US country 8 | [Mercury (Nashville) 172118] written by Robert John "Mutt" Lange & Shania Twain |
|
 | 3. | 04/1999 | | 182
 | US 23 UK 3 US AC 16 US country 4 | [R] [album cut] written by Robert John "Mutt" Lange & Shania Twain |
| 4. | 09/1999 | | 142
 | US 5 UK 70 US AC 9 US country 62 | as Chris Gaines [Capitol 58788] written by Gordon Kennedy, Wayne Kirkpatrick & Tommy Sims |
| 5. | 12/1999 | | 128
 | US 7 US AC 3 US country 49 US R&B 57 | [instrumental] written by traditional |
 | 6. | 04/1999 | | 101
 | US 10 US country ✫1 | [Curb 73080] written by Rodney Crowell & Will Jennings |
 | 7. | 08/1999 | | 68
 | US 24 US AC 21 US country ✫1 | [RCA album cut] written by Keith Follesé, Adrienne Follesé & Tammy Hyler |
 | 8. | 02/1999 | | 65
 | US 27 US country ✫1 | [BNA 65666] written by Tony Mullins & Wendell Mobley |
| 9. | 06/1999 | | 63
 | US 24 US country ✫1 | written by Marv Green, Chris Lindsey & Aimee Mayo |
| 10. | 06/1999 | | 62
 | US 28 US country 2 | [album cut] written by Randy Goodrum & Brent Maher |
| 11. | 08/1999 | | 61
 | US 28 US country ✫1 | [album cut] written by Rick Ferrell & Keith Follesé |
 | 12. | 11/1999 | | 60
 | US 29 US country ✫1 | [album cut] written by Bill Luther & Aimee Mayo |
| 13. | 04/1999 | | 57
 | US 27 US country ✫1 | [MCA album cut] written by Dana Hunt (as Dana Hunt Oglesby) & Kent Robbins |
| 14. | 11/1999 | | 57
 | US 27 US country ✫1 | written by Martie Seidel & Marcus Hummon |
| 15. | 10/1999 | | 55
 | US 23 US country 6 | written by Al Anderson & Jeffrey Steele |
 | 16. | 12/1999 | | 55
 | US 39 UK 55 US country ✫1 | written by Keith Follesé & Chris Lindsey |
 | 17. | 03/1999 | | 54
 | US 28 US country 2 | [RCA 65646] written by Andy Griggs & Brett Jones |
 | 18. | 09/1999 | | 53
 | US 31 US country ✫1 | written by Clint Black |
 | 19. | 10/1999 | | 52
 | US 30 US country ✫1 | [Arista Nashville album cut] written by Brad Paisley & Kelley Lovelace |
 | 20. | 05/1999 | | 52
 | US 29 US country 3 | featuring 'N Sync [RCA 65759] written by Carl Sturken & Evan Rogers |
 | 21. | 04/1999 | | 51
 | US 30 US country 2 | [Capitol album cut] written by Bill Anderson & Steve Wariner |
 | 22. | 07/1999 | | 50
 | US 34 US country ✫1 | [album cut] written by Kenny Chesney & Skip Ewing |
 | 23. | 07/1999 | | 49
 | US 39 UK 53 US country 2 | written by Marcus Hummon & Martie Seidel |
| 24. | 03/1999 | | 48
 | US 34 US country ✫1 | [Mercury album cut] written by Skip Ewing, Bill Anderson & Debbie Moore |
 | 25. | 01/1999 | | 48
 | US 34 US country ✫1 | written by Emily Robison & Martie Seidel |
 | 26. | 05/1999 | | 46
 | US 36 US country ✫1 | [MCA 72092] written by Shaye Smith & Carolyn Dawn Johnson |
| 27. | 10/1999 | | 45
 | US 31 US country 3 | [album cut] written by Michael Dulaney & Neil Thrasher |
| 28. | 05/1999 | | 43
 | US 37 US country 2 | [RCA album cut] written by Ed Hill & Tony Martin |
| 29. | 02/1999 | | 42
 | US 38 US country 2 | [Decca 72068] written by Tony Martin & Tim Nichols |
| 30. | 03/1999 | | 40
 | US 37 US country 4 | [Epic album cut] written by Radney Foster |
 | 31. | 01/1999 | | 39
 | US 39 US country 3 | [Warner 17136] written by Connie Harrington & Bonnie Baker |
 | 32. | 07/1999 | | 38
 | US 39 US country 3 | [Arista album cut] written by Alan Jackson |
| 33. | 10/1999 | | 37
 | US 45 US country 2 | [album cut] written by Arlos Smith & Sara Light |
 | 34. | 05/1999 | | 36
 | US 38 US country 6 | [Epic 79118] written by Max T. Barnes & T. W. Hale |
 | 35. | 01/1999 | | 36
 | US 38 US country 4 | [MCA 72084] written by Wayland Holyfield & Fred Knoblock |
 | 36. | 05/1999 | | 35
 | US 43 US country 3 | [Lyric Street 64025] written by Jason Deere, Kenny Greenberg & Kristyn Osborn |
 | 37. | 07/1999 | | 34
 | US 49 US AC 6 US country 13 | [album cut] written by Robert John "Mutt" Lange & Shania Twain |
| 38. | 09/1999 | | 33
 | US 42 US country 3 | [R] [Capitol album cut] written by Steve Wariner & Steve Ryan |
 | 39. | 01/1999 | | 33
 | US 46 US country 3 | [Mercury album cut] written by Bob Regan & George Teren |
 | 40. | 06/1999 | | 32
 | US 46 US country 4 | [album cut] written by Gretchen Peters |
| 41. | 09/1999 | | 32
 | US 45 US country 4 | [MCA album cut] written by Jim Lauderdale & Melba Montgomery |
 | 42. | 07/1999 | | 32
 | US 46 US country 5 | [Columbia (Nashville) 79210] written by Bill McCorvey, Dave Gibson & Greg Crowe |
 | 43. | 03/1999 | | 31
 | US 43 US country 4 | [Arista album cut] written by Alan Jackson |
| 44. | 06/1999 | | 31
 | US 64 UK 43 US country 12 | [Reprise album cut] written by Freddie Mercury |
 | 45. | 11/1999 | | 30
 | US 43 US country 6 | written by Nat Stuckey |
| 46. | 10/1999 | | 30
 | UK 26 US country 62 | with Vince Gill
written by Richard Marx |
| 47. | 03/1999 | | 30
 | US 47 US country 5 | [Epic album cut] written by D. Vincent Williams & Jim Collins |
 | 48. | 01/1999 | | 29
 | US 51 US country 5 | [Arista album cut] written by Ronnie Dunn & Terry McBride |
| 49. | 04/1999 | | 29
 | US 41 US country 9 | [Asylum 64052] written by Robin Lee Bruce & Matt Hendrix |
 | 50. | 02/1999 | | 29
 | US 44 US country 6 | [Curb 73075] written by Mark Miller, Gregg Hubbard & Mike Lawler |
 | 51. | 05/1999 | | 29
 | US 46 US country 6 | written by Mary Francis, Johnny MacRae & Bob Morrison |
 | 52. | 09/1999 | | 27
 | US 55 US country 8 | [Monument 79248] written by Tim Hunt |
| 53. | 01/1999 | | 27
 | US 50 US country 6 | [album cut] written by Al Anderson & Mary Sharon Rice (as Sharon Vaughn) |
| 54. | 10/1999 | | 25
 | US 58 US country 6 | [R] [album cut] written by Robert John "Mutt" Lange & Shania Twain |
| 55. | 05/1999 | | 24
 | US 54 US country 7 | [album cut] written by David Malloy, Gary Baker & Frank J. Myers |
 | 56. | 09/1999 | | 23
 | US 60 US country 7 | [Mercury album cut] written by Keith Stegall & Dan Hill |
| 57. | 1999 | | 22
 | US country ✫1 | written by Jim Funk & Eric Hickenlooper |
 | 58. | 08/1999 | | 21
 | US 65 US country 10 | [album cut] written by Diane Warren |
 | 59. | 10/1999 | | 20
 | US 76 US country 11 | written by Skip Ewing & Jimmy Wayne (as Jimmy Wayne Barber) |
 | 60. | 06/1999 | | 20
 | US 65 US country 12 | [Arista 13156] written by Brad Paisley, Chris DuBois & Frank Rogers |
| 61. | 10/1999 | | 20
 | US 65 US country 10 | [RCA album cut] written by Zack Turner, Lonnie Wilson & Andy Griggs |
 | 62. | 03/1999 | | 20
 | US 62 US country 13 | [Columbia (Nashville) 79115] written by Bobby Taylor, Mike Geiger & Woody Mullis |
 | 63. | 11/1999 | | 19
 | US 74 US country 11 | [album cut] written by Jim Collins & Paul Overstreet |
 | 64. | 09/1999 | | 19
 | US 76 US country 12 | [album cut] written by Houston Robert & Rivers Rutherford |
 | 65. | 12/1999 | | 19
 | US 74 US country 11 | written by Gary Nicholson & Allen Shamblin |
| 66. | 08/1999 | | 19
 | US 72 US country 12 | [album cut] written by Tony Lane, Jess Brown & David Lee |
| 67. | 03/1999 | | 18
 | US 68 US country 12 | [album cut] written by Tim Gaetano & A. J. Masters |
| 68. | 04/1999 | | 18
 | US 69 US country 12 | [Mercury album cut] written by Bob Regan & Karen Staley |
| 69. | 07/1999 | | 18
 | US 86 US country 19 | [Warner 16984] written by Kelly Garrett, John Hadley & Chad Brock |
| 70. | 01/1999 | | 17
 | US 64 US country 19 | [Epic 79064] written by Robin Lerner, Franne Golde & Steve Booker |
| 71. | 10/1999 | | 16
 | US 83 US country 18 | [Epic 79269] written by Lewis Anderson & Bob Regan |
| 72. | 06/1999 | | 16
 | US 71 US country 15 | [album cut] written by Jeffrey Steele & Danny Wells |
| 73. | 08/1999 | | 16
 | US 75 US country 15 | [Arista album cut] written by John Waite, Mark Leonard & Chas Sandford |
 | 74. | 06/1999 | | 16
 | US 74 US country 16 | [Giant album cut] written by Richie McDonald, Ed Hill & Phil Barnhart |
| 75. | 05/1999 | | 14
 | US 81 US country 16 | [DreamWorks album cut] written by Skip Ewing & Kim Wiliams |
 | 76. | 11/1999 | | 14
 | US 82 US country 16 | [DreamWorks album cut] written by Gary Burr, Robin Lerner & Franne Golde |
| 77. | 06/1999 | | 14
 | US 85 US country 22 | [Columbia 79148] written by Mary Chapin Carpenter, Beth Nielsen Chapman & Annie Roboff |
| 78. | 05/1999 | | 13
 | US 86 US country 17 | written by Keith Stegall & Dan Hill |
 | 79. | 06/1999 | | 13
 | US 82 US country 20 | [Mercury (Nashville) 870818] written by Chuck Cannon, Toby Keith & Kostas |
| 80. | 07/1999 | | 13
 | US 89 US country 29 | [Arista 13140] written by Sherrié Austin & Greg Barnhill |
| 81. | 05/1999 | | 13
 | US 87 US country 17 | [album cut] written by Aaron Barker, Ron Harbin & David Lewis |
| 82. | 01/1999 | | 11
 | US 88 US country 26 | [Columbia 79031] written by Deryl Dodd & Kenny Beard |
| 83. | 12/1999 | | 11
 | US 75 US country 30 | written by Hank Williams Jr. |
 | 84. | 12/1999 | | 11
 | US 61 US country 37 | [Lyric Street 164036] written by traditional |
 | 85. | 04/1999 | | 11
 | US 96 US country 21 | [Epic album cut] written by Blair Daly, Will Rambeaux & Kent Blazy |
| 86. | 06/1999 | | 11
 | US 101 US country 17 | [Decca 72090] written by Daryl Burgess & Tim Johnson |
| 87. | 11/1999 | | 11
 | US 105 US country 19 | written by Ronnie Dunn & Terry McBride |
 | 88. | 12/1999 | | 10
 | US 105 US country 18 | [Capitol 58799] written by Keith Urban & Monty Powell |
| 89. | 07/1999 | | 10
 | US 105 US country 19 | [album cut] written by Danny Orton & Tony Ramey |
| 90. | 11/1999 | | 10
 | US 110 US country 24 | [RCA 65935] written by Mark Collie, Hillary Kanter & Even Stevens |
| 91. | 1999 | | 9
 | US country 12 | |
| 92. | 10/1999 | | 9
 | US 119 US country 27 | written by Chet Biggers & Frank Rogers |
| 93. | 08/1999 | | 9
 | US 113 US country 24 | as Chris Gaines written by Gordon Kennedy, Wayne Kirkpatrick & Tommy Sims |
| 94. | 03/1999 | | 9
 | US 108 US country 28 | written by Rick Bowles, Josh Leo & Tom Shapiro |
| 95. | 03/1999 | | 9
 | US 113 US country 27 | [Arista 13158] written by Walt Aldridge & Brad Crisler |
| 96. | 07/1999 | | 9
 | US 117 US country 25 | written by Kerry Chater, Lynn Gillespie Chater & Cyril Rawson |
 | 97. | 09/1999 | | 8
 | US 111 US country 24 | [Mercury 562291] written by Bob DiPiero, Craig Wiseman & Dan Truman |
| 98. | 1999 | | 8
 | US country 16 | |
| 99. | 1999 | | 7
 | US country 18 | |
| 100. | 03/1999 | | 7
 | US 115 US country 27 | written by Vince Gill & Reed Nielsen |