ATP 250 · 1990-02-05 · draw of 32
Milan 1990
CarpetFinal
| 🇺🇸 Ivan Lendl | d. | 🇺🇸 Tim Mayotte | 6-3 6-2 | H2H |
Semifinals
| 🇺🇸 Tim Mayotte | d. | 🇺🇸 John McEnroe | 6-4 6-4 | H2H |
| 🇺🇸 Ivan Lendl | d. | 🇺🇸 Pete Sampras | 3-6 6-0 6-3 | H2H |
Quarterfinals
| 🇺🇸 Pete Sampras | d. | 🇨🇿 Milan Srejber | 6-7 6-4 6-4 | H2H |
| 🇺🇸 Tim Mayotte | d. | 🇨🇭 Jakob Hlasek | 7-5 6-7 7-5 | H2H |
| 🇺🇸 John McEnroe | d. | 🇩🇪 Eric Jelen | 6-3 6-3 | H2H |
| 🇺🇸 Ivan Lendl | d. | 🇺🇸 Jim Courier | 6-2 6-4 | H2H |
Round of 16
| 🇺🇸 Pete Sampras | d. | 🇩🇪 Markus Zoecke | 6-1 7-6 | H2H |
| 🇩🇪 Eric Jelen | d. | 🇦🇹 Horst Skoff | 7-6 4-5 RET | H2H |
| 🇨🇭 Jakob Hlasek | d. | 🇬🇧 Jeremy Bates | 6-3 3-6 6-3 | H2H |
| 🇺🇸 Jim Courier | d. | 🇨🇿 Karel Novacek | 6-4 6-4 | H2H |
| 🇺🇸 Tim Mayotte | d. | 🇫🇷 Thierry Champion | 6-2 6-1 | H2H |
| 🇨🇿 Milan Srejber | d. | 🇺🇸 Aaron Krickstein | 6-2 6-3 | H2H |
| 🇺🇸 John McEnroe | d. | 🇮🇹 Paolo Cane | 6-4 6-1 | H2H |
| 🇺🇸 Ivan Lendl | d. | 🇷🇺 Alexander Volkov | 6-2 2-6 6-1 | H2H |
Round of 32
| 🇷🇺 Alexander Volkov | d. | 🇮🇹 Simone Colombo | 6-1 6-4 | H2H |
| 🇨🇿 Milan Srejber | d. | 🇮🇹 Stefano Pescosolido | 7-5 6-2 | H2H |
| 🇦🇹 Horst Skoff | d. | 🇮🇹 Paolo Pambianco | 6-2 6-2 | H2H |
| 🇺🇸 Pete Sampras | d. | 🇸🇪 Anders Jarryd | 6-1 6-3 | H2H |
| 🇨🇿 Karel Novacek | d. | 🇫🇷 Jerome Potier | 6-4 6-4 | H2H |
| 🇩🇪 Eric Jelen | d. | 🇳🇱 Paul Haarhuis | 6-4 6-2 | H2H |
| 🇨🇭 Jakob Hlasek | d. | 🇸🇪 Peter Lundgren | 7-6 7-5 | H2H |
| 🇫🇷 Thierry Champion | d. | 🇨🇿 Petr Korda | 6-4 7-6 | H2H |
| 🇮🇹 Paolo Cane | d. | 🇭🇷 Bruno Oresar | 7-6 6-4 | H2H |
| 🇺🇸 Jim Courier | d. | 🇳🇱 Mark Koevermans | 6-2 6-1 | H2H |
| 🇩🇪 Markus Zoecke | d. | 🇺🇸 Jimmy Connors | 6-3 4-6 7-6 | H2H |
| 🇺🇸 Tim Mayotte | d. | 🇨🇿 Martin Strelba | 6-1 6-1 | H2H |
| 🇬🇧 Jeremy Bates | d. | 🇫🇷 Yannick Noah | 7-5 6-4 | H2H |
| 🇺🇸 Aaron Krickstein | d. | 🇮🇹 Omar Camporese | 6-4 6-3 | H2H |
| 🇺🇸 John McEnroe | d. | 🇷🇺 Andrei Cherkasov | 6-1 4-6 6-4 | H2H |
| 🇺🇸 Ivan Lendl | d. | 🇮🇹 Diego Nargiso | 6-3 6-3 | H2H |