He beat out runner-up, Omawumi Megbele getting 63% of the votes. With his victory, he took home many prizes including a recording contract with Sony BMG.
Dakolo was born in Accra, Ghana to a Nigerian father, Bayelsa-native David and a Ghanaian mother, Norah, who died when Dakolo was thirteen. His grandmother Ateni Dakolo, who lived in Port Harcourt raised him, and he credits her as his early singing teacher. Although his parents came to take Dakolo to live with them in Lagos when he was three, Dakolo refused to leave his grandmother.
Dakolo started singing in church at the age of twelve. In 2003 he joined the singing group Purple Love as a founding member. They dominated the Port Harcourt club circuit, but disbanded in 2005 as its members had gained admission into the University of Portharcourt
Before Idol, he won a local talent hunt contest G.E FACTO held in Port Harcourt.
In 2006, Dakolo auditioned for reality show Idols West Africa in Calabar. His songs of choice were Commissioned's More Than I and Lemar's Time to Grow. His vocals impressed the judges, and was seen as a contender for the prize. A week before the viewing of the Top 24 performances, Dakolo received the news that his grandmother had died.
Dakolo first auditioned in Calabar, Cross River State of Nigeria with Commissioned's More Than I and Lemar's Time to Grow. While in the competition, Timi Dakolo was never in the bottom 3. In the final three weeks of the competition it was revealed by the producers of the show that Timi had the highest number of votes each of those weeks.
While in the competition, Timi's grandmother died, a week before the viewing of the Top 24 performances. This was a big emotional blow to him. At that time, he turned to his Christian faith for strength to pull through in the competition. Before going to Idols West Africa, Timi was a student of Communication Studies in the University of Portharcourt
After winning Idol West Africa in 2007, on January 1, 2008, on New Years Day, Timi Dakolo was shot at the lobby of the Presidential Hotel in Port Harcourt. He had gone to the hotel to attend a church service in the company of his friends. The attack was a random act of violence by a faction of Niger Delta militants and did not target Timi. Although a hotel security guard was murdered in the attack, Timi escaped with a flesh wound, was rushed to the hospital, treated and discharged on the same day.
Timi Dakolo released his first single comprising three songs in October 2009.
He is currently signed with Lone Records/Now Muzik.