He was the brains behind three of Singapore's four ASEAN Football Federation (AFF) Suzuki Cup triumphs.
Come November, however, and Raddy Avramovic - now Myanmar national coach - could very well be plotting the Lions' downfall in the tournament.
And the Serb is relishing the prospect of facing his former team.
In a phone interview with The Straits Times, the 64-year-old, who sounded upbeat in his trademark raspy voice, said: "It will be nice to play Singapore in the Suzuki Cup, to come back and see the familiar faces, especially the players I've brought up to the national team.
"Of course, it will be strange to come back and be on the opposite side but there is a job to do on the field."
Co-hosts Singapore are grouped in the opening Suzuki Cup stage with Malaysia, Thailand and the winner of a qualification tournament, widely tipped to be Myanmar, the top-ranked side (world No. 160) among the five teams.
Brunei, Timor-Leste, Laos and Cambodia are the other sides vying for the two available spots.
As recently as two years ago, Avramovic was the toast of the Singapore football fans when he guided the Lions to a record fourth ASEAN title.
During his nine-year tenure, he handed out national debuts to current stalwarts like Safuwan Baharudin, Hariss Harun and Zulfahmi Arifin.
He also appointed Shahril Ishak as national captain four years ago, a position the player still holds today.