Milk is a widely consumed food rich in macro- and micronutrients that play an important role in health preservation. While it affects positively human nutrient and energy uptake, the presence of pesticide residues could, however, counterbalance these benefits and negatively affect human health. This systematic review provides an overview of studies on pesticide residues during the last decade and the related human health risk assessment. Thirty-five original articles published since 2010 reporting the levels of pesticide residues in raw cow's milk in 69 regions from 15 countries were reviewed. Data showed that pesticide residue levels were ranked as, DDTs> permethrin> bifenthrin> Drins> endrin> endosulfan> HCHs> cyhalothrin> cypermethrin> heptachlor> ethion> coumaphos> deltamethrin> dimethoate, chlorpyriphos> profenofos> malathion> dichlorvos> parathion methyl> carbaryl> aldicarb> carbofuran> methamidophos. High geographic variation was observed, and many regions appear as contaminated zones with high risks such as Punjab in Pakistan (× 3080 > MRL and × 113 > MRL for Cypermethrin and Drins, respectively), Sand Pedro in Columbia (× 1090 > MRL and × 200 > MRL for endrin and Drins, respectively), and Gezira State in Sudan (× 109 > MRL DDTs). The risk assessment for humans indicated that HQ Drins values were > 1 in Columbia (Sucre, Casa Azul, San Pedro, Costanera, Sabanas, Sinú Medio, and San Jorge regions), and in Pakistan (Punjab region). Moreover, the HQ values for endrin were > 1 in Sinú Medio (Colombia) and for heptachlor in Costanera region, Sinú Medio, and Sabanas (Colombia). Furthermore, HI values were > 1 in seven regions in Colombia, 1 region in Pakistan, 1 region in Egypt and 1 region in Turkey, suggesting a serious health risk. In conclusion, to avoid cow's milk contamination by pesticides, it is necessary to develop eco-friendly alternatives to chemical pesticides and promote integrated pest management (IPM) strategies.