In 2014, Obermair was promoted to the first team of TSV 1860 Rosenheim. He played in a total of 84 games, scoring 4 goals in his two-year spell with the senior team.
In August 2019, Obermair signed a two-year contract with 3. Liga club Carl Zeiss Jena, joining the club on a free transfer.[6][7] He scored his first and only goal for Carl Zeiss Jena in a 3-2 away defeat against Chemnitzer FC.[8] In June 2020, after playing for one season, it was announced that Obermair have left the club.[9]
Obermair was born and raised in Prien am Chiemsee, Germany to a German father and a Filipino mother, making him eligible to represent either Germany or the Philippines at international level.[15]
In November 2021, Obermair was once again called-up for the Philippines in the 2020 AFF Championship, but was not able to secure a release from his club.[17]