The filamentous fungus Penicillium canescens, isolated from oil-polluted soil, was evaluated for its ability to dissipate high-molecular-weight polycyclic aromatic hydrocarbons (PAH). The study was conducted in a microcosm containing 180 g of historical PAH-contaminated soil under non-sterile conditions with two incubation temperatures (14 °C and 18 °C) on a 12-h cycle. The experiment was conducted over 8 months, with four experimental conditions created by varying the volumes of the bulking agent and vegetable oil (olive oil) and the time of addition of these compounds. The PAH dissipation performance of the fungal augmentation treatment was compared with that achieved with a biostimulated soil (bulking agent and vegetable oil) and with the untreated soil as control. The greatest PAH dissipation was obtained with P. canescens bioaugmentation (35.71% ± 1.73), with 13 of the 16 US EPA PAH significantly dissipated, at rates above 18%, and particularly high-molecular-weight PAH, composed of more than three fused aromatic rings. Nematode toxicity tests indicated a significant decrease in the toxicity of soil bioaugmented by this fungus. Fulvic and humic contents were significantly increased by this treatment. All these results suggest that bioaugmentation with P. canescens can be used to restore soils with long-term PAH contamination.