Chicago 1986 ATP
Final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Boris Becker | m. | Ivan Lendl | 7-6 6-3 |
Semifinal
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Ivan Lendl | m. | Scott Davis | 6-1 7-6 |
| Boris Becker | m. | Jimmy Connors | 7-6 4-6 6-4 |
Perempat final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Ivan Lendl | m. | Johan Kriek | 6-4 6-3 |
| Scott Davis | m. | Kevin Curren | 5-7 7-6 6-4 |
| Boris Becker | m. | Paul Annacone | 6-4 6-4 |
| Jimmy Connors | m. | Andres Gomez | 6-3 6-1 |
Babak 16 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Ivan Lendl | m. | Sammy Giammalva Jr | 6-4 6-3 |
| Johan Kriek | m. | Peter Lindgren | 6-3 6-4 |
| Scott Davis | m. | Tim Mayotte | 6-1 7-6 |
| Kevin Curren | m. | Glenn Michibata | 7-6 6-3 |
| Paul Annacone | m. | Leonardo Lavalle | 6-2 6-1 |
| Boris Becker | m. | John Sadri | 6-4 7-6 |
| Andres Gomez | m. | Larry Stefanki | 6-3 6-2 |
| Jimmy Connors | m. | Robert Seguso | 6-0 6-4 |
Babak 32 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Ivan Lendl | m. | Tim Wilkison | 6-4 6-3 |
| Sammy Giammalva Jr | m. | Bud Schultz | 6-3 6-3 |
| Peter Lindgren | m. | Ramesh Krishnan | 6-2 4-6 6-2 |
| Johan Kriek | m. | Tim Gullikson | 7-5 6-3 |
| Tim Mayotte | m. | Brad Gilbert | 7-6 6-7 6-3 |
| Scott Davis | m. | Peter Fleming | 6-3 6-4 |
| Glenn Michibata | m. | Matt Anger | 6-2 7-6 |
| Kevin Curren | m. | Eliot Teltscher | 6-1 7-6 |
| Paul Annacone | m. | Andrei Chesnokov | 6-3 6-7 6-1 |
| Leonardo Lavalle | m. | Mikael Pernfors | 6-2 6-1 |
| John Sadri | m. | Ricardo Acuna | 7-6 6-3 |
| Boris Becker | m. | Mike Leach | 6-1 6-3 |
| Andres Gomez | m. | Rick Leach | 6-4 7-6 |
| Larry Stefanki | m. | Marty Davis | 6-1 6-4 |
| Robert Seguso | m. | David Pate | 6-3 7-5 |
| Jimmy Connors | m. | Steve Denton | 6-4 6-2 |