The aim of this study is to investigate the difficulties facing Machine Translation (Google) particularly those related to lexis and structure. The researcher has chosen randomly two English and two Arabic texts about various sorts of translation: Media, Scientific, General and Economic. They were taken from several sources (websites, magazine.) to be translated automatically (Google) and humanly from Arabic to English and vice versa. Then they were analyzed to see the challenges that face Machine Translation (Google). The results of the study indicate that MT is problematic and has many challenges concerning lexis such as (Deletions, non-vocalizations, multiple meanings, collocations, additions and acronyms) and syntax like: word order, verb-subject agreement, passive voice etc. On the basis of the results of the study, the researcher recommended that further work needs to be done to create a system that comprises syntax, morphology and semantics of all languages.