Born in Thessaloniki, Kaimakamoudis began his football career with the infrastructure segments of Atromitos in Athens.
[1] He was promoted to Atromitos' first team in 2011, but would not feature in any games during a six-month spell in the 2011−12 Superleague season.
The next season, Kaimakamoudis signed for Gamma Ethniki title contenders Fostiras, narrowly missing out on promotion to the Football League by eventual Group winners OFI Crete.
He then signed for Ergotelis, an ex-Superleague club assembled to swiftly return to professional competitions.
[2] He contributed to Ergotelis' successful championship run with 7 goals in 25 matches, coming in mostly as a back-up striker.