He is believed to have previously been twice on the radar of archrival CSKA Sofia, but then manager Georgi Vasilev deciding on both occasions against securing his services.

[2][3] On 24 October 1997, he played in his first Eternal Derby and scored the winning goal in the 84th minute after a Vladimir Ivanov assist to help the "bluemen" to a 1–0 victory.

[4] In total, Ivanov has participated in 22 editions of the rivalry, scoring a record-breaking 15 goals (the last time he found the net against the "redmen" was in an A PFG match held on 1 November 2008 that finished 1:1).

[6][citation needed] After featuring regularly under the management of Philippe Bergeroo, he saw his opportunities reduced following the former's sacking in October 2002 and the appointment of Vahid Halilhodžić.

Ivanov once again rejoined Levski Sofia on a free transfer from Gaziantepspor in 2006 and won the Bulgarian title for the fourth time in his career.

On 23 July 2009, Ivanov became a manager and head of the sport technical issues in PFC Levski Sofia, but he said that when he is ready he could play again.

After that he returned to Levski Sofia, where he alternated between the positions of head coach and director of football (on occasions also holding them at the same time).

[14] In his capacity as a technical director of the Bulgarian Football Union, he played a role in the decision of employing Mladen Krstajić as the next permanent head coach of Bulgaria.

[15] In January 2023, Ivanov affirmed that as long as he remains in an official capacity with the Football Union, naturalized players of non-Bulgarian origins will not be selected for the national team.