Tour · 1985-04-01 · draw of 32
Chicago 1985
CarpetFinal
| 🇺🇸 John McEnroe | d. | 🇺🇸 Jimmy Connors | W/O | H2H |
Semifinals
| 🇺🇸 Jimmy Connors | d. | 🇪🇨 Andres Gomez | 6-4 6-3 | H2H |
| 🇺🇸 John McEnroe | d. | 🇺🇸 Scott Davis | 6-4 6-1 | H2H |
Quarterfinals
| 🇺🇸 Scott Davis | d. | 🇺🇸 Terry Moor | 6-4 6-4 | H2H |
| 🇪🇨 Andres Gomez | d. | 🇺🇸 Tim Mayotte | 6-3 3-6 6-1 | H2H |
| 🇺🇸 Jimmy Connors | d. | 🇺🇸 Brad Gilbert | 6-4 4-6 7-5 | H2H |
| 🇺🇸 John McEnroe | d. | 🇺🇸 Paul Annacone | 4-6 6-4 6-1 | H2H |
Round of 16
| 🇺🇸 Brad Gilbert | d. | 🇺🇸 Mike Bauer | 6-4 6-1 | H2H |
| 🇺🇸 Scott Davis | d. | 🇺🇸 Bob Green | 6-3 6-4 | H2H |
| 🇺🇸 Tim Mayotte | d. | 🇺🇸 John Sadri | 7-6 7-5 | H2H |
| 🇺🇸 Paul Annacone | d. | 🇺🇸 Johan Kriek | 2-6 7-5 6-4 | H2H |
| 🇺🇸 Terry Moor | d. | 🇫🇷 Yannick Noah | 4-6 7-6 7-6 | H2H |
| 🇪🇨 Andres Gomez | d. | 🇦🇺 John Fitzgerald | 3-6 7-6 6-4 | H2H |
| 🇺🇸 Jimmy Connors | d. | 🇺🇸 David Pate | 6-4 7-6 | H2H |
| 🇺🇸 John McEnroe | d. | 🇺🇸 Mike Leach | 6-1 6-2 | H2H |
Round of 32
| 🇺🇸 John Sadri | d. | 🇺🇸 Todd Witsken | 6-4 7-6 | H2H |
| 🇺🇸 David Pate | d. | 🇺🇸 Todd Nelson | 6-1 6-2 | H2H |
| 🇺🇸 Terry Moor | d. | 🇵🇾 Francisco Gonzalez | 4-6 6-3 6-4 | H2H |
| 🇺🇸 Mike Leach | d. | 🇺🇸 Larry Stefanki | 7-6 6-4 | H2H |
| 🇺🇸 Bob Green | d. | 🇺🇸 Greg Holmes | 6-2 6-4 | H2H |
| 🇺🇸 Brad Gilbert | d. | 🇺🇸 Chip Hooper | 6-1 6-4 | H2H |
| 🇦🇺 John Fitzgerald | d. | 🇺🇸 Ben Testerman | 6-2 7-6 | H2H |
| 🇺🇸 Paul Annacone | d. | 🇺🇸 Leif Shiras | 6-3 7-6 | H2H |
| 🇺🇸 Scott Davis | d. | 🇺🇸 Marty Davis | 6-7 6-3 6-3 | H2H |
| 🇺🇸 Tim Mayotte | d. | Nduka Odizor | 3-6 6-4 7-6 | H2H |
| 🇺🇸 Johan Kriek | d. | 🇺🇸 Sammy Giammalva Jr. | 6-4 6-0 | H2H |
| 🇺🇸 Mike Bauer | d. | 🇺🇸 Eliot Teltscher | 5-7 6-1 6-2 | H2H |
| 🇫🇷 Yannick Noah | d. | 🇺🇸 Mel Purcell | 6-3 6-2 | H2H |
| 🇪🇨 Andres Gomez | d. | 🇺🇸 Juan Farrow | 7-6 4-6 6-3 | H2H |
| 🇺🇸 Jimmy Connors | d. | 🇺🇸 Jay Lapidus | 6-2 6-3 | H2H |
| 🇺🇸 John McEnroe | d. | 🇦🇺 Peter Doohan | 6-0 6-1 | H2H |