List of number-one singles of 1999 (Canada) Chart history Chart history

| Volume_Issue | Issue_Dates | Weeks_on_Top | Song | Artist |
|---|---|---|---|---|
| 68:20-24 | 8 March - 5 April | 5 |  Every Morning  | Sugar Ray |
| 68:25-26 | 12 April - 19 April | 2 |  Love Song  | Sky |
| 69:1-2 | 26 April - 3 May | 2 |  No Scrubs  | TLC |
| 69:3-5 | 10 May - 24 May | 3 |  Kiss Me  | Sixpence None the Richer |
| 69:6-13 | 31 May - 19 July | 8 |  Livin` la Vida Loca  | Ricky Martin |
| 69:14-15 | 26 July - 2 August | 2 |  Beautiful Stranger  | Madonna |
| 69:16-21 | 9 August - 13 September | 6 |  If You Had My Love  | Jennifer Lopez |
| 69:22-26, 70:1-6 | 20 September - 29 November | 11 |  Mambo No. 5  | Lou Bega |
| 70:7 | 6 December | 1 |  Smooth  | Santana featuring Rob Thomas |
| 70:8-9 | 13 December - 3 January 2000 ÷ | 2 ÷ |  Blue  | Eiffel 65 |