This study investigates the level of functional equivalence in the Flood's (2008) translation of two classical Arabic poems into English, a thirty-line poem by al-Mutanabbi and eleven-line poem by Abu Nuwas. The work focuses on how the translator encodes the linguistic, cultural and aesthetic features. These features are examined based on functional equivalence in terms of form and content in the Target Text (TT). The research takes each poem and compares the linguistic, cultural and aesthetic form and content between the Source Text (ST) and Target Text (TT). For the linguistic functional equivalence, the research construes the semantic level in the TT with paying an attention to the schematic and compacted construction of the ST poeticality. In the cultural aspect, on the other hand, the work attempts to locate the area of convergences and divergences between the Arabic and English languages. In the concluding appraisal of each line, the research weighs up between the aesthetic features of the STs and TTs with the purpose of reflecting and maintaining the beauty of classicality, and how this aesthetics goes in conformity with linguistic equivalents. After the appraisal analysis, the work finds that it has become difficult for the translator to capture the linguistic elements as far as classical poetry is concerned; Flood makes the translated lines non-poetic and plain. While the cultural elements are functionally captured in the translation, perhaps because of their rarity in the given poems, the aesthetic features have not been addressed properly. The ST lines were rendered disregarding the beauty and proportional length of the poems. Therefore, for bridging these gaps, the researcher attempts to re-encode these poems and make the two hemistichs of each line to be rhymed and proportionately balanced for having a sense of classical, rather, functional equivalence to the ST.