Osswald spent his youth career with the Columbus Crew Academy before signing a letter of intent to play college soccer at the University of South Florida.
After redshirting his freshman year with the Bulls, Osswald made 13 appearances from 2011 to 2012 before transferring to Xavier University.
Osswald also played in the Premier Development League for Carolina Dynamo, VSI Tampa Flames and Cincinnati Dutch Lions.
[1][2][3] On January 8, 2015, it was announced that Osswald would take part in Major League Soccer's player combine.
He later joined USL expansion side Real Monarchs SLC for the 2015 season and made his professional debut on April 25 in a 1–0 defeat to LA Galaxy II.