| Country: | British Virgin Islands |
| Type: | parliamentary |
| Previous Election: | 1995 British Virgin Islands general election |
| Previous Year: | 1995 |
| Next Election: | 2003 British Virgin Islands general election |
| Next Year: | 2003 |
| Seats For Election: | 13 of the 15 seats in the House of Assembly |
| Majority Seats: | 7 |
| Image1: | D. Orlando Smith (cropped).jpg |
| Leader1: | Orlando Smith |
| Party1: | National Democratic Party (British Virgin Islands) |
| Last Election1: | – |
| Seats1: | 5 |
| Seat Change1: | New |
| Popular Vote1: | 9,126 |
| Percentage1: | 38.14% |
| Leader2: | Ralph T. O'Neal |
| Party2: | Virgin Islands Party |
| Last Election2: | 30.15%, 6 seats |
| Seats2: | 7 |
| Seat Change2: | 1 |
| Popular Vote2: | 8,790 |
| Percentage2: | 36.74% |
| Chief Minister | |
| Posttitle: | Chief Minister after election |
| Before Election: | Ralph T. O'Neal |
| Before Party: | Virgin Islands Party |
| After Election: | Ralph T. O'Neal |
| After Party: | Virgin Islands Party |
General elections were held in the British Virgin Islands on 17 May 1999. The result was a victory for the incumbent Virgin Islands Party (VIP) led by Chief Minister Ralph T. O'Neal over the newly formed National Democratic Party (NDP) led by Orlando Smith.
The elections marked the emergence of the NDP, the first serious opposition to the VIP since the collapse of the United Party in the aftermath of Cyril Romney's resignation as Chief Minister in 1986. They were also the first elections in the territory since 1954 in which Lavity Stoutt, a dominant political force in the British Virgin Islands did not participate and the first in which no independent candidates were elected.[1]
The election was largely decided in three key seats: the Third District (which Julian Fraser carried for the VIP by 26 votes), the Sixth District (which Omar Hodge carried for the VIP by 12 votes) and the Eighth District (which Lloyd Black carried for the NDP by 11 votes, with the crucial Penn family votes being split between Andre (running as an independent) and David (running for the VIP) – most years a member of the Penn family wins the Eighth District). The At-large seats were split equally between the two main parties. Ethlyn Smith won the Fifth District for the minority party, the Concerned Citizens Movement, where the second placed candidate was former Chief Minister running as an independent, Cyril Romney.
Although the overall vote count was flattering to the NDP this was because they polled well in the At-large seats (where each voter casts four votes). But most of the Territorial seats were not that competitive, with the VIP winning some seats with huge majorities, the largest being Alvin Christopher's thumping 80.2% of the vote in the Second District. Conversely, Julian Fraser won his seat in the Third District with the smallest mandate of any candidate – just 228 votes in a three-way contest with a low voter turnout.
Notable candidates who were elected to the Legislature for the first time included future Chief Minister and Premier, Orlando Smith; future Deputy Premier and Minister Kedrick Pickering; future Minister Andrew Fahie; and future Minister and Leader of the Opposition Julian Fraser. Conversely, Walwyn Brewley suffered the first electoral defeat of his career, and would thereafter choose to end his political career at this point.