[3] During the summer of 2012, Bouchalakis earned the trust of manager Siniša Gogić and became a regular starter for the club during their short tenure in the Greek Football League.

Bouchalakis was instrumental in helping the club return to the Superleague at the end of the 2012–13 season, summing up 40 caps in both the Football League and Greek Cup competitions and managing to score 6 goals while supplying two assists.

After Bouchalakis' and Tzanakakis' transfers were announced by Olympiacos, the club's board of directors decided to green-light the loan deal with Ergotelis, who added both players to their roster for the 2013–14 Superleague season in order for them to receive substantial playing time in top-flight in a familiar environment.

[9] After a trial in pre-season, Bouchalakis signed a 3-year contract with EFL Championship club Nottingham Forest in July 2017.

[citation needed] On 23 August 2018, he scored with a header from Kostas Fortounis' free kick to help Olympiacos beat Burnley 3–1 at home in the first leg of the 2018–19 Europa League play-off round; it was his first goal in UEFA competitions.