Tour · 1986-03-24 · draw of 32
Chicago 1986
CarpetFinal
| 🇩🇪 Boris Becker | d. | 🇺🇸 Ivan Lendl | 7-6 6-3 | H2H |
Semifinals
| 🇩🇪 Boris Becker | d. | 🇺🇸 Jimmy Connors | 7-6 4-6 6-4 | H2H |
| 🇺🇸 Ivan Lendl | d. | 🇺🇸 Scott Davis | 6-1 7-6 | H2H |
Quarterfinals
| 🇺🇸 Scott Davis | d. | 🇺🇸 Kevin Curren | 5-7 7-6 6-4 | H2H |
| 🇩🇪 Boris Becker | d. | 🇺🇸 Paul Annacone | 6-4 6-4 | H2H |
| 🇺🇸 Jimmy Connors | d. | 🇪🇨 Andres Gomez | 6-3 6-1 | H2H |
| 🇺🇸 Ivan Lendl | d. | 🇺🇸 Johan Kriek | 6-4 6-3 | H2H |
Round of 16
| 🇺🇸 Scott Davis | d. | 🇺🇸 Tim Mayotte | 6-1 7-6 | H2H |
| 🇪🇨 Andres Gomez | d. | 🇺🇸 Larry Stefanki | 6-3 6-2 | H2H |
| 🇺🇸 Johan Kriek | d. | 🇸🇪 Peter Lindgren | 6-3 6-4 | H2H |
| 🇺🇸 Kevin Curren | d. | 🇨🇦 Glenn Michibata | 7-6 6-3 | H2H |
| 🇺🇸 Paul Annacone | d. | 🇲🇽 Leonardo Lavalle | 6-2 6-1 | H2H |
| 🇩🇪 Boris Becker | d. | 🇺🇸 John Sadri | 6-4 7-6 | H2H |
| 🇺🇸 Jimmy Connors | d. | 🇺🇸 Robert Seguso | 6-0 6-4 | H2H |
| 🇺🇸 Ivan Lendl | d. | 🇺🇸 Sammy Giammalva Jr. | 6-4 6-3 | H2H |
Round of 32
| 🇺🇸 Larry Stefanki | d. | 🇺🇸 Marty Davis | 6-1 6-4 | H2H |
| 🇺🇸 Robert Seguso | d. | 🇺🇸 David Pate | 6-3 7-5 | H2H |
| 🇺🇸 John Sadri | d. | 🇨🇱 Ricardo Acuna | 7-6 6-3 | H2H |
| 🇨🇦 Glenn Michibata | d. | 🇺🇸 Matt Anger | 6-2 7-6 | H2H |
| 🇸🇪 Peter Lindgren | d. | 🇮🇳 Ramesh Krishnan | 6-2 4-6 6-2 | H2H |
| 🇲🇽 Leonardo Lavalle | d. | 🇸🇪 Mikael Pernfors | 6-2 6-1 | H2H |
| 🇺🇸 Sammy Giammalva Jr. | d. | 🇺🇸 Bud Schultz | 6-3 6-3 | H2H |
| 🇺🇸 Scott Davis | d. | 🇺🇸 Peter Fleming | 6-3 6-4 | H2H |
| 🇪🇨 Andres Gomez | d. | 🇺🇸 Rick Leach | 6-4 7-6 | H2H |
| 🇺🇸 Johan Kriek | d. | 🇺🇸 Tim Gullikson | 7-5 6-3 | H2H |
| 🇺🇸 Kevin Curren | d. | 🇺🇸 Eliot Teltscher | 6-1 7-6 | H2H |
| 🇺🇸 Paul Annacone | d. | 🇷🇺 Andrei Chesnokov | 6-3 6-7 6-1 | H2H |
| 🇺🇸 Tim Mayotte | d. | 🇺🇸 Brad Gilbert | 7-6 6-7 6-3 | H2H |
| 🇩🇪 Boris Becker | d. | 🇺🇸 Mike Leach | 6-1 6-3 | H2H |
| 🇺🇸 Jimmy Connors | d. | 🇺🇸 Steve Denton | 6-4 6-2 | H2H |
| 🇺🇸 Ivan Lendl | d. | 🇺🇸 Tim Wilkison | 6-4 6-3 | H2H |