ATP 250 · 1991-02-25 · draw of 32
Chicago 1991
CarpetFinal
| 🇺🇸 John McEnroe | d. | 🇺🇸 Patrick McEnroe | 3-6 6-2 6-4 | H2H |
Semifinals
| 🇺🇸 Patrick McEnroe | d. | 🇨🇦 Grant Connell | 4-6 6-4 6-4 | H2H |
| 🇺🇸 John McEnroe | d. | 🇺🇸 MaliVai Washington | 7-6(6) 6-7(3) 6-4 | H2H |
Quarterfinals
| 🇺🇸 Patrick McEnroe | d. | 🇺🇸 Richey Reneberg | 6-1 7-6(3) | H2H |
| 🇨🇦 Grant Connell | d. | 🇵🇪 Jaime Yzaga | 6-4 6-4 | H2H |
| 🇺🇸 MaliVai Washington | d. | 🇩🇪 Udo Riglewski | 4-6 6-3 6-0 | H2H |
| 🇺🇸 John McEnroe | d. | 🇩🇪 Alexander Mronz | W/O | H2H |
Round of 16
| 🇺🇸 Richey Reneberg | d. | 🇺🇸 David Pate | 6-3 7-6(2) | H2H |
| 🇺🇸 Patrick McEnroe | d. | 🇻🇪 Nicolas Pereira | 6-4 7-6(3) | H2H |
| 🇨🇦 Grant Connell | d. | 🇧🇷 Luiz Mattar | 6-1 6-7(3) 6-3 | H2H |
| 🇵🇪 Jaime Yzaga | d. | 🇺🇸 Kevin Curren | 6-1 3-6 6-4 | H2H |
| 🇩🇪 Udo Riglewski | d. | 🇫🇮 Veli Paloheimo | 7-6(6) 6-3 | H2H |
| 🇺🇸 MaliVai Washington | d. | 🇨🇿 Petr Korda | 6-4 7-6(5) | H2H |
| 🇩🇪 Alexander Mronz | d. | 🇿🇦 Gary Muller | 7-6(6) 6-3 | H2H |
| 🇺🇸 John McEnroe | d. | 🇮🇳 Ramesh Krishnan | 7-5 6-3 | H2H |
Round of 32
| 🇺🇸 Richey Reneberg | d. | 🇺🇸 Todd Martin | 2-6 7-6(4) 6-3 | H2H |
| 🇺🇸 David Pate | d. | 🇲🇽 Luis Herrera | 6-3 6-2 | H2H |
| 🇻🇪 Nicolas Pereira | d. | 🇺🇸 Ken Flach | 6-7(6) 7-5 6-4 | H2H |
| 🇺🇸 Patrick McEnroe | d. | 🇺🇸 Brad Pearce | 6-1 6-7(7) 7-6(4) | H2H |
| 🇧🇷 Luiz Mattar | d. | 🇿🇦 Grant Stafford | 6-3 6-3 | H2H |
| 🇨🇦 Grant Connell | d. | 🇺🇸 Jim Grabb | 6-1 6-4 | H2H |
| 🇵🇪 Jaime Yzaga | d. | 🇺🇸 Jimmy Connors | 6-3 6-0 | H2H |
| 🇺🇸 Kevin Curren | d. | 🇪🇸 Tomas Carbonell | 6-3 6-7(3) 6-2 | H2H |
| 🇫🇮 Veli Paloheimo | d. | 🇺🇾 Marcelo Filippini | 6-3 2-6 6-2 | H2H |
| 🇩🇪 Udo Riglewski | d. | 🇺🇸 Scott Davis | 6-3 7-6(0) | H2H |
| 🇺🇸 MaliVai Washington | d. | 🇸🇰 Marian Vajda | 6-1 6-1 | H2H |
| 🇨🇿 Petr Korda | d. | 🇸🇪 Peter Lundgren | 7-6(5) 6-1 | H2H |
| 🇿🇦 Gary Muller | d. | 🇫🇷 Jean-Philippe Fleurian | 6-4 6-4 | H2H |
| 🇩🇪 Alexander Mronz | d. | 🇺🇸 Michael Robertson | 6-2 6-1 | H2H |
| 🇮🇳 Ramesh Krishnan | d. | 🇫🇮 Aki Rahunen | 6-1 6-4 | H2H |
| 🇺🇸 John McEnroe | d. | 🇮🇱 Gilad Bloom | 6-2 6-1 | H2H |