Philadelphia Union once again will spend preseason in Clearwater, Florida. The team will make two trips south prior to the start of the 2019 season, with the first running from January 28 to February 7 and the second lasting from February 11 until February 24. During the club's second visit to Florida, from February 11-24, the Union will tune up for their upcoming MLS campaign with three preseason games.
In addition, the Union will host a youth soccer clinic on February 19 that will be open to both local clubs and any Union fans that make the trip down to Clearwater and a Fan Event on February 21 that includes a lunch with players after they train. Kickoff times for the Union's preseason games and start times for both the Youth Clinic and Fan Event will be announced closer to the start of preseason.
- February 16 – Game 1
- February 19 – Youth Soccer Clinic
- February 20 – Game 2
- February 21 – Fan Event (lunch with players after training)
- February 23 – Game 3