The European food legislation authorizes the use of certain health claims based on a scientific basis. This study aimed to evaluate the fatty acid, tocopherol, and polar phenol composition of virgin olive oil (VOO) from cv. Chondrolia Chalkidikis and Chalkidiki regarding the fulfillment of official requirements for the health claims of ‘oleic acid’, ‘vitamin E’, and ‘olive oil polyphenols’. The examination of representative industrial VOOs from 15 olive mills of the Chalkidiki regional unit showed that the two cultivars yield oils contained the necessary concentrations of the responsible bioactive compounds. This evidence was further substantiated by a four harvest study whereby olives from different maturity stages were sampled from three olive groves. Oils were extracted at a laboratory scale and examined for their content in the above-mentioned three categories of constituents. Oils produced at industrial scale from olives harvested on the ‘technological optimum’ stage according to the olive grove proprietor were also analyzed. Extra virgin olive oil of the studied cultivars can safely bear the generic claims for ‘oleic acid’ and ‘vitamin E’. The cultivars present great potential regarding the total hydroxytyrosol and tyrosol content of the extracted oil required to attain the third health claim that may be influenced negatively by manufacturing practices.