His first professional job came when Panetolikos F.C., who was participating in Gamma Ethniki, offered Kalaitzidis a contract.
After taking a two-year break, Kalaitzidis returned to the football pitches as he joined ILTEX Lykoi F.C..
After an incredible start, Veria won three matches in a row in the first three fixtures, playing an offensive and beautiful style of football.
Although, Veria secured her return to Superleague early, something that was against any odd for that season, Kalaitzidis, would quit his post after a 1–0 away defeat (the fifth in till that day out of the six in overall) against Thrasyvoulos as Arvanitidis got furious, entered the dressing room and he start blaming the players for the defeat.
In the end of the season, Kalaitzidis, resigned from Veria post due to the incident that took place after the match against Thrasyvoulos, but achieved his second career promotion from Football League to Superleague.
Veria replaced Kalaitzidis with Makis Chavos who was later fired, after the first two fixtures in 2012–13 Superleague Greece season.
He brought back his offensive style of football and achieved to save Veria from relegation for the first time in Superleague after the 1996–97 season.
Although, he was doing great, but after a defeat against Ethnikos Achna part of the fans disapproved him and he decided to leave the club.
The administration board of Nea Salamina wishes to its friend Dimitris Kalaitzidis, any future success to his coaching career as well as any personal and family happiness".
[13] Though, the signing of Spyros Gogolos made by Galanos, a temporary president of the club, led Kalaitzidis to quit his post as he was never notified or even asked about that move.
[16] After his departure from Aris, Kalaitzidis would return to the team again in January 2015, this time as a technical director of the football department.
As a result of that action, Dimitris Kalaitzidis was appointed to the technical director's position in order to run the club as his brother lives in the States.
He's brother is Kosmas Kalaitzidis (Alex Kalas), an American-based businessman who was the head of football department of Aris.