By Nathan Morley in Nicosia
In the first round last weekend, Anastasiades took 35.5 percent of the vote, with Malas gaining 30.2 percent. Turnout was just 71.88 percent, marking a new low point in voter participation.
Unlike in previous years, the ongoing division of the island is not front and centre of campaigns. Instead Anastasiades, 71, has focused on recent economic progress and pressing domestic issues like the creation of a National Health Service.
He also highlighted his handling of the financial recovery which followed a 2013 EU - IMF bailout which saw the forced closure of the islands second largest bank.
His opponent, independent candidate Stavros Malas, has the backing of the left-wing AKEL party. At 50, he is considered to be a youngster on the political scene, but has cabinet experience, having served briefly as Minister of Health under former President Demitris Christofias.
Regarding stalled negotiations to end the four-decade long division of Cyprus, both candidates have expressed a desire to resume dialogue with the Turkish Cypriots after UN-sponsored talks collapsed last year.
Malas is critical of the way Anastasiades conducted talks on behalf of the Greek Cypriot community, charging that he made blunders in the negotiations, which ultimately failed.
A buffer zone cuts this island in two, between Greek and Turkish Cypriot areas. The fenced partition has been in place since Turkey sent its troops to occupy its northern part in response to a coup by the military rulers of Greece in 1974.