Chicago 1985 ATP
Final
| Winner | Loser | Score | |
|---|---|---|---|
| John McEnroe | d. | Jimmy Connors | W/O |
Semifinals
| Winner | Loser | Score | |
|---|---|---|---|
| John McEnroe | d. | Scott Davis | 6-4 6-1 |
| Jimmy Connors | d. | Andres Gomez | 6-4 6-3 |
Quarterfinals
| Winner | Loser | Score | |
|---|---|---|---|
| John McEnroe | d. | Paul Annacone | 4-6 6-4 6-1 |
| Scott Davis | d. | Terry Moor | 6-4 6-4 |
| Andres Gomez | d. | Tim Mayotte | 6-3 3-6 6-1 |
| Jimmy Connors | d. | Brad Gilbert | 6-4 4-6 7-5 |
Round of 16
| Winner | Loser | Score | |
|---|---|---|---|
| John McEnroe | d. | Mike Leach | 6-1 6-2 |
| Paul Annacone | d. | Johan Kriek | 2-6 7-5 6-4 |
| Terry Moor | d. | Yannick Noah | 4-6 7-6 7-6 |
| Scott Davis | d. | Bob Green | 6-3 6-4 |
| Tim Mayotte | d. | John Sadri | 7-6 7-5 |
| Andres Gomez | d. | John Fitzgerald | 3-6 7-6 6-4 |
| Brad Gilbert | d. | Mike Bauer | 6-4 6-1 |
| Jimmy Connors | d. | David Pate | 6-4 7-6 |
Round of 32
| Winner | Loser | Score | |
|---|---|---|---|
| John McEnroe | d. | Peter Doohan | 6-0 6-1 |
| Mike Leach | d. | Larry Stefanki | 7-6 6-4 |
| Paul Annacone | d. | Leif Shiras | 6-3 7-6 |
| Johan Kriek | d. | Sammy Giammalva Jr | 6-4 6-0 |
| Yannick Noah | d. | Mel Purcell | 6-3 6-2 |
| Terry Moor | d. | Francisco Gonzalez | 4-6 6-3 6-4 |
| Bob Green | d. | Greg Holmes | 6-2 6-4 |
| Scott Davis | d. | Marty Davis | 6-7 6-3 6-3 |
| Tim Mayotte | d. | Nduka Odizor | 3-6 6-4 7-6 |
| John Sadri | d. | Todd Witsken | 6-4 7-6 |
| John Fitzgerald | d. | Ben Testerman | 6-2 7-6 |
| Andres Gomez | d. | Juan Farrow | 7-6 4-6 6-3 |
| Mike Bauer | d. | Eliot Teltscher | 5-7 6-1 6-2 |
| Brad Gilbert | d. | Chip Hooper | 6-1 6-4 |
| David Pate | d. | Todd Nelson | 6-1 6-2 |
| Jimmy Connors | d. | Jay Lapidus | 6-2 6-3 |