Winnetka Challenger, 2019, Challenger 80
| Klahn, Bradley[1] | [USA] | |
| Klahn, Bradley[1] | ||
| Young, Donald[15] | [USA] | 61 63 |
| Smith, Roy | [USA] | |
| Fratangelo, Bjorn[6] | ||
| Fratangelo, Bjorn[6] | [USA] | 63 63 |
| Istomin, Denis[4] | [UZB] | |
| Istomin, Denis[4] | ||
| Altamirano, Collin | [USA] | 63 60 |
| Aragone, Jc | [USA] | |
| Ramanathan, Ramkumar[8] | ||
| Ramanathan, Ramkumar[8] | [IND] | 76(6) 63 |
| Jung, Jason[5] | [TPE] | |
| Jung, Jason[5] | ||
| Pervolarakis, Michail (ITF) | [GRE] | 62 64 |
| Kokkinakis, Thanasi[13] | [AUS] | |
| Kokkinakis, Thanasi[13] | ||
| Andreozzi, Guido[3] | [ARG] | 76(5) 40 Ret'd |
| Kozlov, Stefan | [USA] | |
| Kubler, Jason[12] | ||
| Kubler, Jason[12] | [AUS] | 62 63 |
| Eubanks, Christopher[14] | [USA] | |
| Eubanks, Christopher[14] | ||
| Escobedo, Ernesto | [MEX] | 76(2) 64 |
| Klahn, Bradley[1] | [USA] | |
| Klahn, Bradley[1] | ||
| Fratangelo, Bjorn[6] | [USA] | 64 76(3) |
| Istomin, Denis[4] | [UZB] | |
| Istomin, Denis[4] | ||
| Ramanathan, Ramkumar[8] | [IND] | 62 75 |
| Jung, Jason[5] | [TPE] | |
| Kokkinakis, Thanasi[13] | ||
| Kokkinakis, Thanasi[13] | [AUS] | 76(4) 61 |
| Kubler, Jason[12] | [AUS] | |
| Kubler, Jason[12] | ||
| Eubanks, Christopher[14] | [USA] | 64 63 |
| Klahn, Bradley[1] | [USA] | |
| Klahn, Bradley[1] | ||
| Istomin, Denis[4] | [UZB] | 62 63 |
| Kokkinakis, Thanasi[13] | [AUS] | |
| Kubler, Jason[12] | ||
| Kubler, Jason[12] | [AUS] | w/o |
| Klahn, Bradley[1] | [USA] | |
| Klahn, Bradley[1] | ||
| Kubler, Jason[12] | [AUS] | 62 75 |
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