Ajiboye began his career with Prime F.C., and in September 2008 joined Wikki Tourists F.C. After one year with Wikki Tourists, where he played 14 games, he left on 16 September 2009 to sign with the Spanish club Pontevedra CF.
After being released from Pontevedra in November 2011, he signed the next month with Shooting Stars.
After 3SC's relegation in 2013, he signed to play for Nasarawa United. However, transfer issues kept him from playing until two months in the new season.