He worked as a teacher for some time, then was admitted to Fourah Bay College, Sierra Leone in 1943, obtaining a Bachelor of Arts degree in English, Modern History and Economics in June, 1946.

In December 1962, he left Imade College to become founder, proprietor and first principal of Owo High School from January 1963 to August, 1975, when he retired.

Omoboriowo later fell out with him, and switched to the National Party of Nigeria (NPN), where he competed against Ajasin in the 1983 elections and was initially declared winner.

[7] Ajasin held office until the military coup of 31 December 1983 that brought General Muhammadu Buhari to power.

I had two personal cars at the time I assumed office but left without any: one had ended its serviceable lifespan with its use for the shadow elections in 1982, while the other was borrowed by a political associate with whom it ended up its lifespanIn 2000, during the government of Chief Adebayo Adefarati, a new university was created in Akungba Akoko and later named Adekunle Ajasin University in his honour.

The coalition was formed to bring an end to the military government of Sani Abacha and the regime to honour the electoral mandate given to MKO Abiola.