 After undergoing a 2018–19 season-ending right ankle surgery, for a peroneal tendon rupture, on 1 April 2019, Spanoulis began individual workouts again on 5 July 2019.After his return to individual training, Spanoulis signed a one year contract extension with Olympiacos, at a salary of €600,000 net income.On 29 November 2019, Spanoulis passed Juan Carlos Navarro, to become the EuroLeague's all-time career leader in Performance Index Rating (PIR).