Psaila began his career at
Ħamrun Spartans in 1910, where he helped them win two league titles. Psaila helped the team win the
1918–19 Maltese First Division, in the team's only league season. He spent the
1920–21 season at newly-formed
Marsa United, before joining the
Malta Police football team, which he helped create. At Malta Police, he was considered one of the team's star players for the
1921–22 season, and was the team's
captain. In 1922, he signed for
Floriana, where he became Malta's first ever professional footballer. Psaila spent three seasons at Floriana, where he helped them win the Cassar Cup in 1923 and the Maltese First Division in the
1924–25 season, before retiring from football. In 2022, Psaila was chosen by the
IFFHS for their Malta all-time men's dream team. ==International career==