The list of number-one singles of 1999 in Italy includes all the songs that reached the top spot on the weekly chart compiled by the Federazione Industria Musicale Italiana (FIMI).

Chart history WeekSingleArtist(s)Ref.1"Believe"Cher23456"Pretty Fly (For a White Guy)"The Offspring78910"Oggi sono io"Alex Britti11"...Baby One More Time"Britney Spears12"Snow on the Sahara"Anggun13"...Baby One More Time"Britney Spears1415"Flat Beat"Mr. Oizo16"Snow on the Sahara"Anggun17"Per te"Jovanotti18"I Want It That Way"Backstreet Boys1920212223"Beautiful Stranger"Madonna24"Unforgivable Sinner"Lene Marlin25"Il mio nome è mai più"Liga-Jova-Pelù26272829303132333435363738394041"New Day"Wyclef Jean featuring Bono42"Il mio nome è mai più"Liga-Jova-Pelù43"50 special"Lùnapop4445"Keep On Movin'"Five46"La fine del millennio"Vasco Rossi474849505152

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