Kaimakoglou began his professional career with the
Greek League club
Near East during the 2002–03 season. In 2004, he moved to the Greek club
Maroussi. He was named to the
Greek League Best Five in 2010. He joined the Greek club
Panathinaikos in July 2010. With Panathinaikos, Kaimakoglou won the
EuroLeague and Greek League championships in 2011. He also won the
Greek Cup title with Panathinaikos in 2012. In July 2012, he signed a two-year contract with the Russian
VTB United League club
UNICS Kazan, at an amount of 2.4 million
euros net income. In July 2014, he extended his contract with UNICS for two more years. On June 12, 2016, he re-signed with UNICS for one more season. Kaimakoglu averaged 4.6 points, 3.3 rebounds and 1.5 assists per game during the 2019–20 season. He re-signed with the team on September 19, 2020. On September 10, 2021, Kaimakoglou announced his retirement from professional basketball. ==National team career==