1999 Colonial Classic – Draw
| Draw | |
|---|---|
| 1999 Colonial Classic | |
| Champion |  Thomas Enqvist | 
| Runner-up | .svg.png) Mark Philippoussis | 
| Score | 6–4, 6–1 | 
Mark Philippoussis was the defending Tennis champion, but Thomas Enqvist defeated him 6–4, 6–1, in the final.
Players
 Andre Agassi (semifinals, third place) Andre Agassi (semifinals, third place)
 Tim Henman (first round, eighth place) Tim Henman (first round, eighth place)
 Yevgeny Kafelnikov (first round, fifth place) Yevgeny Kafelnikov (first round, fifth place)
 Goran Ivanišević (first round, withdrew due to a back injury) Goran Ivanišević (first round, withdrew due to a back injury)
 Petr Korda (first round, sixth place) Petr Korda (first round, sixth place)
.svg.png) Mark Philippoussis (final, second place) Mark Philippoussis (final, second place)
 Thomas Enqvist (champion, first place) Thomas Enqvist (champion, first place)
 Michael Chang (semifinals, fourth place) Michael Chang (semifinals, fourth place)
 Mikael Tillström (replaced Goran Ivanišević, seventh place) Mikael Tillström (replaced Goran Ivanišević, seventh place)
Draw
Key
- Q = Qualifier
- WC = Wild card
- LL = Lucky loser
- Alt = Alternate
- ITF = ITF entry
- PR = Protected ranking
- SR = Special ranking
- SE = Special exempt
- JE = Junior exempt
- JR = Junior Accelerator Programme entrant
- CO = College Accelerator Programme entrant
- NG = Next Gen Accelerator Program entrant
- w/o = Walkover
- r = Retired
- d = Defaulted
Main draw
| First round | Semifinals | Final (First/Second place match) | ||||||||||||||||||
| 1 |  Andre Agassi | 6 | 6 | |||||||||||||||||
| 5 |  Petr Korda | 2 | 1 | |||||||||||||||||
| 1 |  Andre Agassi | 3 | 61 | |||||||||||||||||
| 7 |  Thomas Enqvist | 6 | 77 | |||||||||||||||||
| 4 |  Goran Ivanišević | 64 | 65 | |||||||||||||||||
| 7 |  Thomas Enqvist | 77 | 77 | |||||||||||||||||
| 7 |  Thomas Enqvist | 6 | 6 | |||||||||||||||||
| 6 | .svg.png) Mark Philippoussis | 4 | 1 | |||||||||||||||||
| 6 | .svg.png) Mark Philippoussis | 2 | 6 | 6 | ||||||||||||||||
| 3 |  Yevgeny Kafelnikov | 6 | 4 | 4 | ||||||||||||||||
| 6 | .svg.png) Mark Philippoussis | 62 | 7 | 6 | Third/Fourth place match | |||||||||||||||
| 8 |  Michael Chang | 77 | 5 | 3 | ||||||||||||||||
| 8 |  Michael Chang | 65 | 6 | 7 | 1 |  Andre Agassi | 6 | 6 | ||||||||||||
| 2 |  Tim Henman | 77 | 3 | 5 | 8 |  Michael Chang | 3 | 2 | ||||||||||||
Play-offs
| First round | Fifth/Sixth place match | ||||||||||||
| 5 |  Petr Korda | 711 | 6 | ||||||||||
| 4 |  Goran Ivanišević | 69 | 2 | ||||||||||
| 5 |  Petr Korda | 6 | 1 | 2 | |||||||||
| 3 |  Yevgeny Kafelnikov | 1 | 6 | 6 | |||||||||
| 3 |  Yevgeny Kafelnikov | 6 | 1 | 6 | |||||||||
| 2 |  Tim Henman | 2 | 6 | 2 | Seventh/Eighth place match | ||||||||
| 9 |  Mikael Tillström | 7 | 6 | ||||||||||
| 2 |  Tim Henman | 5 | 1 | ||||||||||