| Country: | Republic of Macedonia |
| Type: | presidential |
| Previous Election: | 1994 Macedonian general election |
| Previous Year: | 1994 |
| Next Election: | 2004 Macedonian presidential election |
| Next Year: | 2004 |
| Election Date: | 31 October 1999 (first round) |
| Turnout: | 65.12% (first round) 69.10% (second round) |
| Image1: | Борис Трайковский (07-03-2002) (cropped).jpg |
| Nominee1: | Boris Trajkovski |
| Party1: | VMRO-DPMNE |
| Popular Vote1: | 582,808 |
| Percentage1: | 53.16% |
| Nominee2: | Tito Petkovski |
| Party2: | Social Democratic Union of Macedonia |
| Popular Vote2: | 513,614 |
| Percentage2: | 46.84% |
| President | |
| Before Election: | Kiro Gligorov |
| Before Party: | Social Democratic Union of Macedonia |
| After Election: | Boris Trajkovski |
| After Party: | VMRO-DPMNE |
Presidential elections were held in Macedonia on 31 October 1999, with a second round on 14 November.[1] Tito Petkovski of the Social Democratic Union won the first round. However, as he received less than 50% of the vote, the election went to a second round, which was won by Boris Trajkovski of VMRO-DPMNE, who won 53.2% of the vote.