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Polyhedral oligomeric silsesquioxane grafting thermally conductive silicon carbide particle (POSS-g-SiCp) fillers, are performed to fabricate highly thermally conductive ultra high molecular weight polyethylene (UHMWPE) composites combining with optimal dielectric properties and excellent thermal stabilities, via mechanical ball milling followed by hot-pressing method. The POSS-g-SiCp/UHMWPE composite with 40 wt% POSS-g-SiCp exhibits relative higher thermal conductivity, lower dielectric constant and more excellent thermal stability, the corresponding thermally conductive coefficient of 1.135 W/mK, the dielectric constant of 3.22, and the 5 wt% thermal weight loss temperature of 423 °C, which holds potential for packaging and thermal management in microelectronic devices. Agari’s semi-empirical model fitting reveals POSS-g-SiCp fillers have strong ability to form continuous thermally conductive networks.