Tour · 1969-09-08 · draw of 16
Chicago 1969
CarpetFinal
| 🇦🇺 Ken Rosewall | d. | 🇺🇸 Earl Butch Buchholz | 6-3 6-4 | H2H |
Semifinals
| 🇦🇺 Ken Rosewall | d. | 🇫🇷 Pierre Barthes | 8-1 | H2H |
| 🇺🇸 Earl Butch Buchholz | d. | 🇪🇸 Andres Gimeno | 8-5 | H2H |
Quarterfinals
| 🇦🇺 Ken Rosewall | d. | 🇺🇸 Ron Holmberg | 8-4 | H2H |
| 🇪🇸 Andres Gimeno | d. | 🇬🇧 Roger Taylor | 8-7 | H2H |
| 🇺🇸 Earl Butch Buchholz | d. | 🇿🇦 Raymond Moore | 8-7 | H2H |
| 🇫🇷 Pierre Barthes | d. | 🇺🇸 Marty Riessen | 8-5 | H2H |
Round of 16
| 🇬🇧 Roger Taylor | d. | 🇦🇺 Roy Emerson | 8-6 | H2H |
| 🇦🇺 Ken Rosewall | d. | 🇩🇰 Torben Ulrich | 8-2 | H2H |
| 🇺🇸 Marty Riessen | d. | 🇿🇦 Cliff Drysdale | 8-4 | H2H |
| 🇿🇦 Raymond Moore | d. | 🇦🇺 Tony Roche | 8-6 | H2H |
| 🇺🇸 Ron Holmberg | d. | 🇦🇺 Fred Stolle | 8-5 | H2H |
| 🇪🇸 Andres Gimeno | d. | 🇳🇱 Tom Okker | 7-5 4-6 6-2 | H2H |
| 🇺🇸 Earl Butch Buchholz | d. | 🇭🇷 Nikola Pilic | 8-6 4-6 6-2 | H2H |
| 🇫🇷 Pierre Barthes | d. | 🇦🇺 John Newcombe | 8-6 | H2H |