Tour · 1969-03-31 · draw of 64
San Juan 1969
HardFinal
| 🇺🇸 Arthur Ashe | d. | 🇺🇸 Charlie Pasarell | 5-7 5-7 6-0 6-4 6-3 | H2H |
Semifinals
| 🇺🇸 Charlie Pasarell | d. | 🇸🇪 Ove Nils Bengtson | 11-9 6-2 | H2H |
| 🇺🇸 Arthur Ashe | d. | 🇨🇱 Jaime Fillol Sr. | 6-4 6-3 | H2H |
Quarterfinals
| 🇺🇸 Charlie Pasarell | d. | 🇦🇺 Bill Bowrey | 6-4 6-4 | H2H |
| 🇨🇱 Jaime Fillol Sr. | d. | 🇨🇿 Jan Kodes | 3-6 6-4 6-3 | H2H |
| 🇸🇪 Ove Nils Bengtson | d. | 🇳🇿 Brian Fairlie | 1-6 6-3 6-3 | H2H |
| 🇺🇸 Arthur Ashe | d. | 🇺🇸 Tom Edlefsen | 3-6 6-1 6-2 | H2H |
Round of 16
| 🇺🇸 Charlie Pasarell | d. | 🇪🇬 Ismail El Shafei | 6-3 6-4 | H2H |
| 🇨🇿 Jan Kodes | d. | 🇺🇸 Ron Holmberg | 6-3 6-4 | H2H |
| 🇨🇱 Jaime Fillol Sr. | d. | 🇧🇷 Thomaz Koch | 6-4 3-6 6-3 | H2H |
| 🇳🇿 Brian Fairlie | d. | 🇭🇷 Zeljko Franulovic | 6-2 6-0 | H2H |
| 🇺🇸 Tom Edlefsen | d. | 🇬🇧 Mark Cox | 7-5 6-3 | H2H |
| 🇦🇺 Bill Bowrey | d. | 🇩🇪 Ingo Buding | 6-4 6-2 | H2H |
| 🇸🇪 Ove Nils Bengtson | d. | 🇺🇸 Stan Smith | 7-5 6-4 | H2H |
| 🇺🇸 Arthur Ashe | d. | 🇷🇸 Nicola Spear | 7-5 6-4 | H2H |
Round of 32
| 🇷🇸 Nicola Spear | d. | 🇧🇷 Jose Edison Mandarino | 6-2 6-0 | H2H |
| 🇺🇸 Stan Smith | d. | 🇮🇪 Michael Hickey | 6-2 3-6 6-4 | H2H |
| 🇺🇸 Charlie Pasarell | d. | 🇨🇴 Jairo Velasco Sr. | 9-7 6-1 | H2H |
| 🇨🇿 Jan Kodes | d. | 🇺🇸 E. Victor Seixas | 6-3 6-4 | H2H |
| 🇧🇷 Thomaz Koch | d. | 🇬🇧 Gerald Battrick | 6-8 6-3 10-8 | H2H |
| 🇺🇸 Ron Holmberg | d. | 🇷🇴 Ilie Nastase | 6-2 2-6 6-4 | H2H |
| 🇭🇷 Zeljko Franulovic | d. | 🇨🇿 Milan Holecek | 9-7 9-7 | H2H |
| 🇨🇱 Jaime Fillol Sr. | d. | 🇦🇺 John Alexander | 6-0 8-6 | H2H |
| 🇳🇿 Brian Fairlie | d. | 🇦🇺 Ray Ruffels | 6-3 6-1 | H2H |
| 🇪🇬 Ismail El Shafei | d. | 🇨🇴 Ivan Molina | W/O | H2H |
| 🇺🇸 Tom Edlefsen | d. | 🇨🇴 William Alvarez | 7-5 6-4 | H2H |
| 🇬🇧 Mark Cox | d. | Richard Russell | 6-3 6-4 | H2H |
| 🇩🇪 Ingo Buding | d. | Oscar Rene Cruz | 6-3 6-2 | H2H |
| 🇦🇺 Bill Bowrey | d. | 🇩🇪 Hans-Joachim Ploetz | 8-6 3-6 6-3 | H2H |
| 🇸🇪 Ove Nils Bengtson | d. | 🇨🇱 Luis Ayala | 7-5 7-5 | H2H |
| 🇺🇸 Arthur Ashe | d. | 🇺🇸 Morton Stern | 6-2 6-0 | H2H |
Round of 64
| 🇺🇸 Stan Smith | d. | 🇳🇿 Onny Parun | 6-3 9-11 6-4 | H2H |
| 🇺🇸 E. Victor Seixas | d. | Bobby Odasz | 6-2 6-3 | H2H |
| 🇷🇴 Ilie Nastase | d. | Freddie De Jesus | 7-5 6-4 | H2H |
| 🇨🇿 Jan Kodes | d. | 🇦🇺 Phil Dent | 6-4 6-4 | H2H |
| 🇺🇸 Ron Holmberg | d. | 🇬🇧 Peter Curtis | 6-0 6-3 | H2H |
| 🇮🇪 Michael Hickey | d. | Juan Alberto Rios | 6-3 6-3 | H2H |
| 🇸🇪 Ove Nils Bengtson | d. | Juan Ortiz | 6-1 6-0 | H2H |
| 🇨🇱 Luis Ayala | d. | 🇺🇸 Hamilton Ham Richardson | 6-3 4-6 6-2 | H2H |