The rapid growth of dairy sectors in the Middle East, particularly in Lebanon, led to extensive use of antibiotics to enhance the health and productivity of animals. Prolonged usage may lead to antibiotic residues in foods of animal origin; hence, the emergence of antimicrobial resistant microorganisms. Accurate data on the antibiotic usage in livestock treatment, antibiotic residues and antimicrobial resistances in raw milk in Lebanon are lacking. This study aimed to investigate the types and usages of antibiotics in cattle, their residual levels and the potential microbial resistances in raw milk samples. A questionnaire-based survey identified Gentamicin and Streptomycin as the most frequently used antibiotics. Selected raw milk samples from main dairy farms were then analyzed in duplicate by quantitative ELISA for the antibiotics residual levels. The mean residual levels of Gentamicin and Streptomycin were 90 and 80 μg/L, respectively; which are below the allowable maximum residue limit of 200 μg/L as set by the FAO/WHO. Staphylococcus aureus, Listeria monocytogenes, E. coli and total aerobic microorganisms isolated from the milk samples were then tested for resistance against Gentamicin and Streptomycin by the disc agar diffusion method. All the S. aureus, E. coli, and L. monocytogenes isolates showed high resistance to Gentamicin. However, 95% of S. aureus, 60% of E. coli and 58% of L. monocytogenes isolates were resistant to Streptomycin. The obtained results provide evidence that antimicrobial resistant strains of the above pathogens have become remarkably widespread in raw milk. This requires better management for antibiotic usages among livestock farmers to control sources of food contamination and reduce the health risks associated with the development of resistant microbial strains.