After ending one of MLS’s longest postseason droughts, the Chicago Fire hope to achieve a milestone triumph on Wednesday night. Hosting Orlando City in the Eastern Conference wild-card game, the Fire aim to secure their first playoff victory in 16 years.

In a milestone match, the Chicago Fire secured a 2-0 win over CF Montreal at Stade Saputo, marking their seventh road victory of the 2025 season. Philip Zinckernagel made history during this temperate summer night showdown.

Tom Barlow notched his first career MLS hat trick, scoring his initial three goals of the season, as the Chicago Fire dominated D.C. United 7-1 on Saturday night.