Jonathan Holland is renowned in the local football community. He has played for Malta a total of 18 times at the senior level during his playing career.
At the Senior level nationally, he made almost 300 appearances and scored 55 goals. This includes his participation in UEFA tournaments with the teams he represented, primarily Floriana and Birkirkara, as well as his time spent playing for Ħamrun Spartans. Jonathan spent a brief amount of time abroad as well, working for Conference League teams Bradford Park AFC and Nairn County FC in the north of Scotland.