Home History
| Italy Serie D | 2019/09/29 13:00 | Virtus Ciserano Bergamo v Pro Sesto | W | 1-2 |
| Italy Serie D | 2019/09/22 13:00 | Pro Sesto v Tritium | D | 1-1 |
| Italy Serie D | 2019/09/15 13:00 | Virtus Bolzano v Pro Sesto | W | 1-2 |
| Italy Serie D | 2019/09/11 18:30 | Pro Sesto v ASD Brusaporto | W | 3-1 |
| Italy Serie D | 2019/09/07 13:00 | Dro v Pro Sesto | L | 2-1 |
| Italy Serie D | 2019/09/01 13:00 | Pro Sesto v Arconatese | W | 3-1 |
| Europe Friendlies | 2019/07/31 15:00 | US Pergolettese v Pro Sesto | W | 1-2 |
| Italy Serie D | 2019/05/19 14:00 | Mantova v Pro Sesto | W | 1-2 |
Away History
| Italy Serie D | 2019/09/29 13:00 | USD Castellanzese v Caravaggio | D | 0-0 |
| Italy Serie D | 2019/09/22 13:00 | Scanzorosciate v USD Castellanzese | L | 1-0 |
| Italy Serie D | 2019/09/14 13:00 | USD Castellanzese v Bustese Milano City | W | 3-1 |
| Italy Serie D | 2019/09/11 13:00 | US Inveruno v USD Castellanzese | L | 2-0 |
| Italy Serie D | 2019/09/07 14:00 | USD Castellanzese v US Folgore Caratese | L | 1-2 |
| Italy Serie D | 2019/09/01 13:00 | US Levico Terme v USD Castellanzese | L | 3-1 |
| Europe Friendlies | 2019/08/07 16:00 | SC Caronnese v USD Castellanzese | L | 3-2 |