Philadelphia Union's 2026 roster decisions will be complex due to MLS's calendar transition. The team must navigate contract expirations and roster changes amidst a new season format. The MLS calendar transition will move from a Spring-Summer-Fall season to a Fall-Winter-Spring season. This change will create a one-time seven-month hole in the schedule, from December 18th, 2026 to mid-July 2027. The team will need to adapt to this new format and make roster decisions accordingly. The team's management will need to consider contract expirations, player performance, and team needs when making roster decisions. The team's fans will be eager to see how the team navigates this new format and makes the necessary roster changes to remain competitive.