In away leg ended 3-0 (Liberopoulos, Moras and Sapanis scored) and at home ended 1-0 with Tsouklis' goal.
On 4 January 2009, he made his professional debut for PAS Giannina in a match against Agrotikos Asteras.
Kouroupis started his career in the youth ranks of Agrotikos Asteras before moving to Cretan club Irodotos.