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