| Cover | | Date  | Title • Artist  Album | Points  | Charts Peaks | Comment |
|---|
 | 1. | 09/1999 | | 188
 | US 10 UK 5 | [Jive 42606] written by Jörgen Elofsson, Per Magnusson, David Kreuger & Max Martin |
 | 2. | 04/1999 | | 146
 | US 8 UK 31 US R&B 4 | co-produced by R. Kelly [Track Masters 78857] written by R. Kelly |
|
 | 3. | 05/1999 | | 156
 | UK ✫1 US dance 7 | written by ATB (as André Tanneberger) |
| 4. | 01/1999 | | 136
 | UK ✫1 | written by Bobby Gosh |
| 5. | 02/1999 | | 136
 | US 9 UK 23 US dance 4 US R&B 3 | featuring Puff Daddy [Bad Boy 79203] written by Diddy (as Sean Combs), Schon-Jamel Crawford, Faith Evans, T. Gaither, R. Lawrence, B.J. Reed, T. Russaw & G. Underwo |
 | 6. | 05/1999 | | 193
 | US 4 UK 24 US alt. 2 | [album cut] written by Greg Camp |
 | 7. | 10/1999 | | 271
 | US 6 UK 2 US alt. ✫1 | written by Mark Hoppus & Tom DeLonge |
 | 8. | 12/1999 | | 240
 | US ✫1 UK 21 US AC 2 | [R] written by Marv Green, Chris Lindsey & Aimee Mayo |
| 9. | 12/1999 | | 128
 | US 7 US AC 3 US country 49 US R&B 57 | [instrumental] written by traditional |
 | 10. | 08/1999 | | 188
 | US 2 US AC 4 US R&B 7 | [Motown 156501] written by Brian McKnight |
 | 11. | 07/1999 | | 305
 | US ✫1 UK 4 US AC 14 US dance ✫1 | [Overbrook 97122] written by Paul Barry & Mark Taylor |
| 12. | 06/1999 | | 196
 | US 19 UK 2 US AC 23 US dance ✫1 | Not commercially released in the U.S. [album cut] written by Madonna & William Orbit |
| 13. | 07/1999 | | 173
 | US 27 UK 2 US dance 3 | as DJ Jürgen presents Alice DeeJay written by Sebastiaan Molijn (as Pronti) & Eelke Kalberg (as Kalmani) |
 | 14. | 06/1999 | | 284
 | US ✫1 UK 6 US dance 13 US R&B ✫1 | [Columbia 79175] written by Kevin "She'kspere" Briggs (as Kevin Briggs), Kandi (as Kandi Burruss), Beyoncé (as Beyoncé Knowles), LeToya Luckett & Kelly Rowland |
 | 15. | 03/1999 | | 136
 | UK ✫1 | written by Martin Brannigan, Ray Hedges, Tracey Ackerman & Andy Caine |
 | 16. | 09/1999 | | 286
 | US 6 UK ✫1 US dance 6 | written by Jeffrey Jey, Maurizio Lobina & Massimo Gabutti |
 | 17. | 06/1999 | | 152
 | US 84 UK ✫1 US dance 13 | written by Dennis Van Den Driesschen (as Danski) & Wessel Van Diepen (as DJ Delmundo) |
 | 18. | 11/1999 | | 288
 | US 2 UK 33 US AC ✫1 US country ✫1 | [Warner 16884] written by Stephanie Bentley & Holly Lamar |
 | 19. | 06/1999 | | 138
 | UK ✫1 | written by Eliot Kennedy, Tim Lever, Mike Percy & S Club 7 |
 | 20. | 10/1999 | | 147
 | US 4 US R&B 15 | featuring 'Nsync [Track Masters album cut] written by Billy Lawrence, LeShan Lewis, Corey Rooney, V. Ruby, William Shelby, Kevin Spencer, Nidra Sylvers & L. Van Horssen |
 | 21. | 09/1999 | | 187
 | US 3 UK 28 US AC 21 US dance 12 | [Latin Grammy Award for Song of the Year 2000] written by Marc Anthony & Cory Rooney |
| 22. | 03/1999 | | 155
 | US 45 UK ✫1 US AC 27 | [spoken] [Capitol 58764] written by Mary Schmich, Nigel Swanston & Tim Cox |
 | 23. | 12/1999 | | 209
 | US ✫1 UK 42 US alt. 5 | [RCA 65981] written by Matt Scannell |
 | 24. | 01/1999 | | 168
 | US 21 UK 4 US R&B 7 | [Ruffhouse album cut] written by Lauryn Hill, Alan Bergman, Marilyn Bergman, Marvin Hamlisch, RZA (as Robert Diggs), Ghostface Killah (as Dennis Coles), G. Grice & Raekwon (as Corey Woods) |
| 25. | 04/1999 | | 144
 | UK ✫1 | written by Mr. Oizo (as Quentin Dupieux) |
 | 26. | 10/1999 | | 138
 | UK ✫1 | [UK Record of the Year 1999] written by Wayne Hector & Steve Mac |
 | 27. | 04/1999 | | 160
 | US 4 US R&B ✫1 | produced by R. Kelly [Rock Land 79135] written by R. Kelly |
 | 28. | 07/1999 | | 345
 | US ✫1 UK ✫1 | [RCA 65692] written by Steve Kipner, David Frank & Pam Sheyne |
 | 29. | 10/1999 | | 207
 | US 4 UK 15 US R&B ✫1 | written by Montell Jordan, Brian Palmer, Darren Benbow, Antoine Lavar Wilson, Jörg Evers, Jürgen Korduletsch (as Jürgen S. Korduletsch) & Sergio Moore |
 | 30. | 11/1999 | | 180
 | US 10 UK 6 | written by Brad Young, Dow Brain & Rich Cronin |
 | 31. | 04/1999 | | 167
 | US 10 UK 5 US dance 35 | [Interscope 97048] written by Jordan Knight, Jimmy Jam (as James Harris III), Terry Lewis & Robin Thicke |
 | 32. | 09/1999 | | 307
 | US ✫1 UK 5 US dance 2 US R&B ✫1 | featuring Jay-Z [Columbia 79260] written by Mariah Carey, Sean Carter, Shirley Elliston, Lincoln Chase, Michael Walden & Jeffrey Cohen |
| 33. | 10/1999 | | 144
 | US 7 US alt. ✫1 | [R] written by Scott Stapp & Mark Tremonti |
| 34. | 11/1999 | | 188
 | US 5 UK 18 US R&B ✫1 | featuring Nas, Eve & Q-Tip Q-Tip appears on the radio version of the Hot Boyz remix, but not the video version written by Missy Elliott, Timbaland, Nas, Eve (as Eve Jeffers) & Q-Tip (as Kamaal Fareed) |
| 35. | 12/1999 | | 156
 | UK ✫1 | written by Benny Andersson, Björn Ulvaeus, Jacques Brel & Rod McKuen |
 | 36. | 10/1999 | | 272
 | US ✫1 UK 10 US AC ✫1 | written by Darren Hayes & Daniel Jones |
| 37. | 01/1999 | | 228
 | US 4 UK 16 US AC 8 US dance ✫1 US R&B 3 | charted as I Still Believe / Pure Imagination in US R&B charts [Columbia 79093] written by Antonina Armato & Giuseppe Cantarelli |
 | 38. | 10/1999 | | 217
 | US 5 UK 7 US AC 21 US R&B 121 | written by Macy Gray, Jeremy Ruzumna, Jinsoo Lim & David Wilder |
 | 39. | 10/1999 | | 226
 | US 3 UK 7 US AC 25 | [Columbia 79262] written by Louis Biancaniello & Sam Watters |
 | 40. | 04/1999 | | 282
 | US 6 UK ✫1 US AC ✫1 | written by Max Martin & Andreas Carlsson |
| 41. | 08/1999 | | 203
 | US 12 UK 2 US AC 24 US R&B 5 | [Jive 42623] written by R. Kelly |
| 42. | 08/1999 | | 137
 | UK ✫1 | written by Jörgen Elofsson, David Kreuger & Per Magnusson |
 | 43. | 05/1999 | | 342
 | US ✫1 UK 4 US dance 5 US R&B 6 | [Work 79163] written by LaShawn Daniels, Fred Jerkins III, Rodney Jerkins & Cory Rooney |
 | 44. | 01/1999 | | 278
 | US 4 UK 3 US dance ✫1 US R&B 7 | [Arista 13681] written by LaShawn Daniels, Toni Estes, Rodney Jerkins, Fred Jerkins III & Isaac Phillips |
 | 45. | 11/1999 | | 139
 | UK ✫1 | written by Richard Stannard, Julian Gallagher, Sean Conlon & Abs Breen |
 | 46. | 11/1999 | | 159
 | UK ✫1 US dance ✫1 | written by Chris Brann |
 | 47. | 09/1999 | | 129
 | US 25 UK 5 | written by Max Martin, Kristian Lundin & Brian Littrell |
 | 48. | 05/1999 | | 203
 | US 2 UK 42 US rock 5 US alt. 2 | [Epic 79197] written by Wayne Cochran, Joe Carpenter, Randall Hoyal & Bobby McGlon |
 | 49. | 11/1999 | | 139
 | UK ✫1 | written by Geri Halliwell, Paul Wilson, Andy Watkins & Tracey Ackerman |
 | 50. | 04/1999 | | 365
 | US ✫1 UK ✫1 US AC 18 US dance 5 | [C2/Columbia 79124] written by Ricky Martin, Desmond Child & Draco Rosa (as Robi Rosa) |
 | 51. | 05/1999 | | 129
 | UK 2 US dance 12 | written by Geri Halliwell, Andy Watkins & Paul Wilson |
| 52. | 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 |
 | 53. | 08/1999 | | 292
 | US 3 UK ✫1 US AC 26 | written by Perez Prado |
 | 54. | 04/1999 | | 182
 | US 23 UK 3 US AC 16 US country 4 | [R] [album cut] written by Robert John "Mutt" Lange & Shania Twain |
 | 55. | 02/1999 | | 153
 | US 82 UK ✫1 US dance 9 | [Logic/Beyond 78040] written by Jimmy Destri |
 | 56. | 08/1999 | | 143
 | UK ✫1 US dance 19 | written by Geri Halliwell, Andy Watkins & Paul Wilson |
 | 57. | 09/1999 | | 192
 | US 2 UK 34 US AC 2 | produced by David Foster written by Diane Warren |
 | 58. | 07/1999 | | 298
 | US 4 UK 2 US dance ✫1 US R&B 2 | written by Jerry Duplessis & Wyclef Jean |
 | 59. | 02/1999 | | 150
 | US 36 UK 2 US R&B 18 US alt. 37 | produced by Dr. Dre [Aftermath 95040] written by Eminem (as Marshall Mathers) & Dr. Dre (as Andre Young) |
 | 60. | 02/1999 | | 356
 | US ✫1 UK 3 US R&B ✫1 | [LaFace 24385] written by Kevin "She'kspere" Briggs, Kandi (as Kandi Burruss) & Tameka "Tiny" Cottle |
 | 61. | 04/1999 | | 146
 | UK ✫1 | written by Jim Marr & Wendy Page |
 | 62. | 01/1999 | | 182
 | US 36 UK ✫1 US alt. 2 | [Astralwerks 66254] written by Fatboy Slim & Camille Yarbrough |
 | 63. | 09/1999 | | 242
 | US 2 UK 8 US R&B ✫1 | as Puff Daddy featuring R. Kelly written by Diddy (as Sean Combs), Jeffrey "J-Dub" Walker, R. Greene, K. Price, R. Kelly, Denzil Foster, Thomas McElroy & Jay King |
 | 64. | 12/1999 | | 319
 | US ✫1 UK 3 US dance 39 US R&B ✫1 | written by Rodney Jerkins, Fred Jerkins III, LaShawn Daniels, Beyoncé (as Beyoncé Knowles), LeToya Luckett, Kelly Rowland (as Kelendria Rowland) & LaTavia Roberson |
 | 65. | 06/1999 | | 211
 | US 9 UK 15 US rock ✫1 US alt. ✫1 | [Warner 16913] written by Flea, John Frusciante, Anthony Kiedis & Chad Smith |
 | 66. | 08/1999 | | 170
 | US 2 US AC 4 | [C2 79259] written by George Noriega, Jon Secada & Draco Rosa (as Robi Rosa) |
 | 67. | 11/1999 | | 137
 | UK ✫1 | [BRIT Awards Best British Single 2000] charted as She's the One/It's Only Us in UK charts written by Karl Wallinger |
 | 68. | 07/1999 | | 380
 | US ✫1 UK 3 US AC 11 US rock 10 US alt. 24 | featuring Rob Thomas
[Grammy Award for Song of the Year 2000]
[Grammy Award for Record of the Year 2000] [Arista 13718] written by Itaal Shur & Rob Thomas |
 | 69. | 06/1999 | | 153
 | US 7 UK 90 US AC 29 US alt. 7 | [Lava 84536] written by David Kahne & Sugar Ray |
 | 70. | 05/1999 | | 163
 | US 21 UK 3 US AC 11 | [album cut] written by Jörgen Elofsson |
 | 71. | 05/1999 | | 189
 | US 9 UK 8 US alt. 5 | based up "more more more - andrea true conn." [Work album cut] written by Marc Costanzo & Gregg Diamond |
 | 72. | 07/1999 | | 187
 | US 3 UK 16 | written by Brad Young, Dow Brain & Rich Cronin |
 | 73. | 09/1999 | | 127
 | UK 3 US dance ✫1 | written by Bob Marley |
 | 74. | 05/1999 | | 194
 | US 20 UK ✫1 US AC 22 | written by Steve Mac & Wayne Hector |
 | 75. | 05/1999 | | 145
 | UK ✫1 | written by Danny Langsman & Steven Meade |
 | 76. | 10/1999 | | 152
 | US 12 UK 25 US dance ✫1 US rock 4 US alt. 3 | written by Richard Patrick |
| 77. | 05/1999 | | 189
 | US 2 UK 40 US R&B 2 | [MCA 55551] written by K-Ci (as Cedric Hailey), JoJo (as Joel Hailey) & Rory Bennett |
 | 78. | 12/1999 | | 252
 | US ✫1 UK 10 US R&B ✫1 | featuring Joe & 98 Degrees [Columbia 79338] written by Mariah Carey, Jimmy Jam (as James Harris III) & Terry Lewis |
 | 79. | 01/1999 | | 238
 | US 7 UK 3 US AC 8 US country 8 | [Mercury (Nashville) 172118] written by Robert John "Mutt" Lange & Shania Twain |
| 80. | 11/1999 | | 197
 | US 6 UK 12 US AC ✫1 | written by Max Martin, Kristian Lundin & Andreas Carlsson |
 | 81. | 11/1999 | | 134
 | US 57 UK 3 US rock 33 US alt. 11 | written by Peter Buck, Mike Mills & Michael Stipe |
| 82. | 03/1999 | | 157
 | US 5 UK 29 US AC 4 | [Universal 156246] written by David Frank & Steve Kipner |
 | 83. | 11/1999 | | 150
 | UK ✫1 | written by traditional |
 | 84. | 09/1999 | | 257
 | US 7 UK 2 US R&B ✫1 | featuring Left Eye [Untouchables 24420] written by Delvis Damon, Eddie Ferrell (as DJ Eddie F), Anthony Hamilton, Darren Lighty, Clifton Lighty (as Cliff Lighty), Lisa "Left Eye" Lopes, Balewa Muhammad & I Willis |
 | 85. | 06/1999 | | 309
 | US ✫1 UK 6 US R&B 4 | [LaFace 24424] written by Dallas Austin & T-Boz (as Tionne Watkins) |
 | 86. | 10/1999 | | 207
 | US 8 UK 5 US dance ✫1 | [Work 79292] written by Maria Christensen, Michael Garvin & Phil Temple |
 | 87. | 02/1999 | | 159
 | US 26 UK 3 US dance 5 | written by Dennis Van Den Driesschen (as Danski) & Wessel Van Diepen (as DJ Delmundo) |
 | 88. | 09/1999 | | 137
 | UK ✫1 | written by Geraint Wyn Hughes & Jeffrey Calvert |
 | 89. | 11/1999 | | 294
 | US ✫1 UK 3 US dance 18 | written by Shelly Peiken & Guy Roche |
 | 90. | 01/1999 | | 246
 | US 3 UK 6 US R&B ✫1 | featuring Janet [Elektra 64051] written by Busta Rhymes (as Trevor Smith), Darrell Allamby & A. Roberson |
| 91. | 08/1999 | | 145
 | UK ✫1 | written by Paul Overstreet & Don Schlitz |
| 92. | 03/1999 | | 144
 | UK ✫1 | [Comic Relief single] written by Wayne Anton Braithwaite, Barry James Eastmond, Robert John "Mutt" Lange & Billy Ocean |
 | 93. | 05/1999 | | 252
 | US 4 UK 22 US R&B 3 | [Motown 860891] written by Missy Elliott (as Melissa Elliott), Eric Seats & Rapture Stewart |
 | 94. | 04/1999 | | 148
 | US 5 US R&B 2 | featuring Solé [Tony Mercedes/Freeworld 53469] written by Tricky Stewart (as Christopher Stewart), JT Money, T. Johnston, Tab & D. Davis |
 | 95. | 01/1999 | | 157
 | US 74 UK 2 US rock 10 US alt. 4 | [album cut] written by Dexter Holland, Noodles, Greg K. & Ron Welty |
 | 96. | 05/1999 | | 310
 | US ✫1 UK 2 US R&B 3 | featuring Dru Hill & Kool Moe Dee based upon "I Wish" by Stevie Wonder [Overbrook 79157] written by Kool Moe Dee (as Moe DeWese), Rob Fusari, Will Smith & Stevie Wonder |
 | 97. | 10/1999 | | 159
 | US 25 UK 2 US R&B 66 | featuring K-Ci [Columbia 79287] written by Robinson, Smith, Bennett & Henson |
 | 98. | 12/1999 | | 151
 | US 35 UK 2 US R&B 13 | featuring Mack 10 & Ms. Toi written by Ice Cube (as O'Shea Jackson) & Mack 10 (as Dedrick Rolison) |
 | 99. | 02/1999 | | 155
 | UK ✫1 US dance 2 | featuring Duane Harden written by Armand Van Helden, Duane Harden & Kossi Gardner |
 | 100. | 05/1999 | | 138
 | UK ✫1 | written by Randy Goodrum |