Jaakkola previously played for TP-47 and FC-88. In the January 2007 window, Jaakkola signed a three-and-a-half-year contract with Serie A side Siena. He made his Serie A debut by substituting Dimitrios Eleftheropoulos in the 2007–08 season final matchday, a 2–2 home draw with Palermo. In 2009, he was loaned to V.F. Colligiana in Lega Pro Seconda Divisione. He moved to Slavia Prague on free transfer in July 2010, signing a two-year contract with the option of a further year.