He made his Serie A debut by substituting Dimitrios Eleftheropoulos in the 2007–08 season final matchday, a 2–2 home draw with Palermo.

He moved to Slavia Prague on free transfer in July 2010, signing a two-year contract with the option of a further year.

[5] In January 2011, Jaakkola left Slavia for Scottish Premier League club Kilmarnock, under the management of fellow Finn Mixu Paatelainen.

Jaakkola joined South African Premier Soccer League club Ajax Cape Town in August 2013.

[17] Jaakkola featured in the first two League Two matches of the 2021–22 season before the return of his recurring Achilles injury forced him out of action.

[20] Following Rovers' promotion back to League One at the end of the 2021–22 season,[21] On 30 August 2010 he was selected to represent Finland for European Championship qualification matches against Moldova and Netherlands as a replacement for injured Peter Enckelman.

He gained his second appearance in the national team on 7 June 2017 when Markku Kanerva announced that Jaakkola would replace Lukáš Hrádecký in a friendly match against Liechtenstein.

[24] Jaakkola was a member of the Finnish squad at the UEFA Euro 2020 tournament but remained as an unused substitute for Lukáš Hrádecký.

[29] In September 2024, Jaakkola was announced to have joined National League side Southend United as goalkeeping coach.