This is a list of the number-one hits of 1999 on Italian Hit Parade Singles Chart.[1]
| Issue Date | Song | Artist(s) |
|---|---|---|
| 2 January | "Iris" | |
| 9 January | "Believe" | Cher |
| 16 January | ||
| 23 January | ||
| 30 January | ||
| 6 February | ||
| 13 February | ||
| 20 February | ||
| 27 February | ||
| 6 March | ||
| 13 March | ||
| 20 March | "Pretty Fly (For a White Guy)" | The Offspring |
| 27 March | "Snow on the Sahara" | Anggun |
| 3 April | "...Baby One More Time" | Britney Spears |
| 10 April | "Pretty Fly (For a White Guy)" | The Offspring |
| 17 April | "...Baby One More Time" | Britney Spears |
| 24 April | ||
| 1 May | "Flat Beat" | Mr. Oizo |
| 8 May | ||
| 15 May | ||
| 22 May | "...Baby One More Time" | Britney Spears |
| 29 May | "I Want It That Way" | |
| 5 June | ||
| 12 June | "Per te" | Jovanotti |
| 19 June | "I Want It That Way" | Backstreet Boys |
| 26 June | ||
| 3 July | "Beautiful Stranger" | Madonna |
| 10 July | "Il mio nome è mai più" | Jovanotti, Ligabue & Piero Pelu |
| 17 July | ||
| 24 July | ||
| 31 July | ||
| 7 August | ||
| 14 August | ||
| 21 August | ||
| 28 August | ||
| 4 September | ||
| 11 September | "Mambo No. 5" | Lou Bega |
| 18 September | ||
| 25 September | ||
| 2 October | ||
| 9 October | ||
| 16 October | ||
| 23 October | "50 Special" | Lùnapop |
| 30 October | ||
| 6 November | ||
| 13 November | ||
| 20 November | "Keep on Movin'" | Five |
| 27 November | "La fine del Millennio" | Vasco Rossi |
| 4 December | ||
| 11 December | ||
| 18 December | ||
| 25 December |