In March 2009, he succeeded his uncle Dimitar Penev as manager of CSKA Sofia and under his guidance the team qualified for the group stages of the UEFA Europa League, defeating FC Dynamo Moscow – 2–1 on aggregate. On 6 November 2009, he gave his resignation, after a 1–3 loss to Swiss side FC Basel due to a conflict with the club's owners. CSKA finished 4th in the group behind Roma, Basel and Fulham. CSKA won its single point in the opening game against the future finalist Fulham (1–1 after a good strike from Michel Platini and a mistake from CSKA goalkeeper Ivan Karadzhov). However, Penev's resignation was not accepted, because the CSKA fans wanted him to stay.