- 2026-10-28 in 2d Orlando City at Chicago Fire
- 2025-05-31 1y Chicago Fire 3 at Orlando City 1 Philip Aksel Frigast Zinckernagel USA-CHIC 84min 1g 2a
- 2025-05-03 1y Orlando City 0 at Chicago Fire 0
- 2023-08-20 3y Orlando City 3 at Chicago Fire 1 Martín Exequiel Ojeda USA-ORHN 11min
- 2023-07-01 3y Chicago Fire 1 at Orlando City 3 Facundo Daniel Torres Pérez USA-ORHN 90min 2g
- 2022-04-09 4y Chicago Fire 0 at Orlando City 1 Ercan Kara USA-ORHN 75min 1g
- 2022-03-05 4y Orlando City 0 at Chicago Fire 0
- 2021-08-21 5y Chicago Fire 0 at Orlando City 1 Mason Stajduhar USA-ORHN 90min
- 2021-07-07 5y Orlando City 1 at Chicago Fire 3 Bobby Shuttleworth USA-CHRU 90min
- 2020-09-19 6y Chicago Fire 1 at Orlando City 4 Luís Carlos Almeida da Cunha USA-ORLA 90min 1g
- 2019-10-06 7y Chicago Fire 5 at Orlando City 2 Przemysław Frankowski USA-CHRU 90min 2g
- 2019-03-09 7y Orlando City 1 at Chicago Fire 1
- 2018-09-16 8y Orlando City 0 at Chicago Fire 4 Nemanja Nikolić USA-CHRU 90min 2g
- 2018-05-26 8y Chicago Fire 2 at Orlando City 1 Aleksandar Katai USA-CHRU 90min 1g
- 2017-06-24 9y Orlando City 0 at Chicago Fire 4 David Accam USA-CHRU 80min 3g
- 2017-06-04 9y Chicago Fire 0 at Orlando City 0
- 2016-08-14 10y Orlando City 2 at Chicago Fire 2
- 2016-03-11 10y Chicago Fire 1 at Orlando City 1
- 2015-09-19 11y Orlando City 1 at Chicago Fire 0 Bryan Giovanni Róchez Mejia USA-ORHN 19min 1g
- 2015-08-29 11y Chicago Fire 1 at Orlando City 1
- 2015-07-23 11y Orlando City 1 at Chicago Fire 3 Chibuike Kennedy Igboananike USA-CHRU 24min 2g
- 2015-06-06 11y Orlando City 3 at Chicago Fire 2 Eric Humberto Ávila USA-ORHN 90min 1a
- 2013-06-27 13y Orlando City 1 at Chicago Fire 5 Chris Rolfe USA-CHRU 80min 2g