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- beauty pageant: Miss South Africa
- edition: 44th
- venue: Sun City Superbowl, Sun City, Moses Kotane, North West, South Africa
- date: December 11, 1999
- candidates: 26
- broadcaster: SABC3
CANDIDATES
- Anele Ndamase (Eastern Cape)
- Ashley Burke (Northern Cape)
- Britta van der Hoek (Eastern Cape)
- Buhle Mthethwa (North West)
- Celeste Smith (Free State)
- Claire Norman (Northern Cape)
- Collette Oliphant (Mpumalanga)
- Gareth Brown (Gauteng)
- Heather Joy Hamilton (KwaZulu-Natal)
- Ilze-Lee Graham (Northern Cape) *withdrew
- Kerry Corlett (North West)
- Kgomotso Chipane (North West)
- Leah Masilela (Northern Province)
- Lonely Pmokane (Mpumalanga)
- Megan du Preez (Mpumalanga)
- Motsehoa Molelekoa (Free State)
- Nadia Wyngaard (Western Cape)
- Natasha Raymond (Western Cape)
- Pulane Moraladi (Gauteng)
- Queen Moedjadji Sithole (Gauteng)
- Saskia Falken (Western Cape)
- Tammey Erasmus (Northern Province)
- Tandiswa Dada (Eastern Cape)
- Tarryn Meaker (KwaZulu-Natal)
- Taryn Thompson (Free State)
- Tintswalo Hoveni (Northern Province)
- Vanessa Naidoo (KwaZulu-Natal)
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SPECIAL AWARD
- Miss Photogenic: Nadia Wyngaard (Western Cape)
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WINNERS
| PLACEMENT | 1999 | 1998 |
| Top 9 | Ashley Burke (Northern Cape) Leah Masilela (Northern Province) Megan du Preez (Mpumalanga) Motsehoa Molelekoa (Free State) | N/A |
| Top 5 | Kgomotso Chipane (North West) Britta van der Hoek (Eastern Cape) | Amanda Ngomane (Northern Province) Marguerite Rabbolini (Eastern Cape) |
| 2nd princess | Pulane Moraladi (Gauteng) | Keziah Jooste (Western Cape) |
| 1st princess | Nadia Wyngaard (Western Cape) | Heidi van Zyl (Gauteng) |
| Miss South Africa | Heather Joy Hamilton (KwaZulu-Natal) | Sonia Raciti (KwaZulu-Natal) |
Categories: Africa, beauty pageant results, LISTS, South Africa
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