Just a year later, Olimpija added another trophy to its collection. On May 30, 2019, under the guidance of coach Safet Hadžić, the Dragons faced Maribor in the Slovenian Cup final in Celje. Thanks to an excellent performance and two goals from Stefan Savić, Olimpija claimed a 2–1 victory. In May 2021, Olimpija once again celebrated a Cup victory. Coach Goran Stanković led the team to a 2–1 triumph over Celje at Bonifika Stadium in Koper. Goals from Đorđe Ivanović and Nik Kapun secured yet another memorable win for the Dragons.

A new important milestone in the club’s history occurred in the fall of 2021 when, after six years at the helm, Milan Mandarić bid farewell to Olimpija. He sold the club to the German businessman Adam Delius, who arrived in Ljubljana with a clear goal: to elevate Olimpija to a significantly higher level, both in terms of results and, above all, organizationally.