This study aims at analysing and assessing translations of oxymorons from English into Arabic. To work towards this aim, the study selects 20 English oxymorons from Shakespeares Romeo and Juliet, in addition to the selection of four different Arabic translations of the same 20 oxymorons as published by four different translators, namely, Enani, Omar, Jamal, and Hussein. The analysis of the translations of the 20 oxymorons is conducted in order to justify the assessments of the translations. The assessments of whether given translations of oxymorons are appropriate or inappropriate are primarily deduced from whether the translations render appropriate or inappropriate effects, respectively. Appropriate or inappropriate effects are also the results of whether the translations have maintained or unmaintained our three proposed semantic and syntactic variables. The three proposed variables of lexical form, syntactic structure, and contradictory meaning are the main contributions of this work, as no other studies include such a set of variables to analyse and assess translations of oxymorons. In addition, preserving these three variables contributes to our main argument in this thesis, which is, adopting a semantic approach to the translation of oxymorons is more convenient than adopting a communicative (pragmatic) one, as the semantic approach is more economical in this case, helps in keeping an unaltered meaning, and produces effects similar to the ones obtained from the original source language. The conclusions show that following a semantic approach to the translation of oxymoron through maintaining the variables of lexical form, syntactic structure, and contradictory meaning results in producing appropriate effects rather than inappropriate ones, and leads to assessments of appropriate translations rather than inappropriate ones.