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