Tour · 1969-02-24 · draw of 16
Curacao 1969
HardFinal
| 🇺🇸 Cliff Richey | d. | 🇬🇧 Mark Cox | 6-4 6-3 6-3 | H2H |
Semifinals
| 🇺🇸 Cliff Richey | d. | 🇦🇺 Ray Ruffels | 5-7 6-1 6-1 | H2H |
| 🇬🇧 Mark Cox | d. | 🇷🇴 Ilie Nastase | 8-6 3-6 6-1 | H2H |
Quarterfinals
| 🇦🇺 Ray Ruffels | d. | 🇩🇪 Ingo Buding | 6-2 6-2 | H2H |
| 🇺🇸 Cliff Richey | d. | 🇸🇪 Ove Nils Bengtson | 6-4 6-2 | H2H |
| 🇷🇴 Ilie Nastase | d. | 🇻🇪 Jorge Andrew | 6-3 1-6 6-1 | H2H |
| 🇬🇧 Mark Cox | d. | 🇨🇿 Jan Kukal | 8-6 4-6 6-3 | H2H |
Round of 16
| 🇦🇺 Ray Ruffels | d. | Kenneth Hennep | 6-0 6-1 | H2H |
| 🇺🇸 Cliff Richey | d. | 🇨🇴 William Alvarez | 6-1 6-1 | H2H |
| 🇷🇴 Ilie Nastase | d. | 🇨🇿 Jan Kodes | 6-4 7-5 | H2H |
| 🇨🇿 Jan Kukal | d. | 🇪🇸 Manuel Orantes | 4-6 6-4 8-6 | H2H |
| 🇬🇧 Mark Cox | d. | 🇻🇪 Amable Plaza | 6-0 6-2 | H2H |
| 🇩🇪 Ingo Buding | d. | 🇧🇷 Jose Edison Mandarino | 1-6 6-4 6-4 | H2H |
| 🇸🇪 Ove Nils Bengtson | d. | 🇺🇸 Tom Edlefsen | 6-2 7-9 6-4 | H2H |
| 🇻🇪 Jorge Andrew | d. | 🇻🇪 Isaias Pimentel | 6-3 6-4 | H2H |