Chicago, IL Challenger, 2023, Challenger 75
| Shimizu, Yuta | [JPN] | |
| Shimizu, Yuta | ||
| Chung, Yunseong (Q) | [KOR] | 63 57 63 |
| Jung, Jason (ALT) | [TPE] | |
| Jung, Jason (ALT) | ||
| Basavareddy, Nishesh | [USA] | 36 76(5) 62 |
| Uchiyama, Yasutaka (ALT) | [JPN] | |
| Lajal, Mark | ||
| Lajal, Mark | [EST] | 46 62 62 |
| Walton, Adam | [AUS] | |
| Mpetshi Perricard, Giovanni[7] | ||
| Mpetshi Perricard, Giovanni[7] | [FRA] | 76(3) 64 |
| Schoolkate, Tristan (Q) | [AUS] | |
| Quinn, Ethan (WC) | ||
| Quinn, Ethan (WC) | [USA] | 46 63 62 |
| Marchenko, Illya (Q) | [UKR] | |
| Shang, Juncheng[4] | ||
| Shang, Juncheng[4] | [CHN] | 75 63 |
| Nishikori, Kei (WC) | [JPN] | |
| Nishikori, Kei (WC) | ||
| Mansouri, Skander (ALT) | [TUN] | 76(1) 64 |
| Michelsen, Alex | [USA] | |
| Michelsen, Alex | ||
| Kovacevic, Aleksandar[2] | [USA] | 64 62 |
| Shimizu, Yuta | [JPN] | |
| Shimizu, Yuta | ||
| Jung, Jason (ALT) | [TPE] | 62 75 |
| Lajal, Mark | [EST] | |
| Mpetshi Perricard, Giovanni[7] | ||
| Mpetshi Perricard, Giovanni[7] | [FRA] | 76(3) 46 76(6) |
| Quinn, Ethan (WC) | [USA] | |
| Shang, Juncheng[4] | ||
| Shang, Juncheng[4] | [CHN] | 75 61 |
| Nishikori, Kei (WC) | [JPN] | |
| Michelsen, Alex | ||
| Michelsen, Alex | [USA] | 76(13) 36 61 |
| Shimizu, Yuta | [JPN] | |
| Shimizu, Yuta | ||
| Mpetshi Perricard, Giovanni[7] | [FRA] | 76(5) 76(5) |
| Shang, Juncheng[4] | [CHN] | |
| Michelsen, Alex | ||
| Michelsen, Alex | [USA] | 46 75 63 |
| Shimizu, Yuta | [JPN] | |
| Michelsen, Alex | ||
| Michelsen, Alex | [USA] | 75 62 |
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