Late wilt disease (LWD) of maize, caused by Magnaporthiopsis maydis, is considered a major threat to commercial fields in Israel, Egypt, Spain, and India. Today’s control methods include chemical and agronomical intervention but rely almost solely on resistant maize cultivars. In recent years, LWD research focused on eco-friendly biological approaches to restrain the pathogen. The current study conducted during two growing seasons explores the potential of three Trichoderma species as bioprotective treatments against LWD. These species excelled in preliminary assays performed previously under controlled conditions and were applied here in the field by directly adding them to each seed with the sowing. In the first field experiment, Trichoderma longibrachiatum successfully rescued the plants’ growth indices (weight and height) compared to T. asperelloides and the non-treated control. However, it had no positive effect on yield and disease progression. In the subsequent season, this Trichoderma species was tested against T. asperellum, an endophyte isolated from susceptible maize cultivar. This experiment was conducted during a rainy autumn season, which probably led to a weak disease burst. Under these conditions, the plants in all treatment groups were vivid and had similar growth progression and yields. Nevertheless, a close symptoms inspection revealed that the T. longibrachiatum treatment resulted in a two-fold reduction in the lower stem symptoms and a 1.4-fold reduction in the cob symptoms at the end of the seasons. T. asperellum achieved 1.6- and 1.3-fold improvement in these parameters, respectively. Quantitative Real-time PCR tracking of the pathogen in the host plants’ first internode supported the symptoms’ evaluation, with 3.1- and 4.9-fold lower M. maydis DNA levels in the two Trichoderma treatments. In order to induce LWD under the autumn’s less favorable conditions, some of the plots in each treatment were inoculated additionally, 20 days after sowing, by stabbing the lower stem section near the ground with a wooden toothpick dipped in M. maydis mycelia. This infection method overrides the Trichoderma roots protection and almost abolishes the biocontrol treatments’ protective achievements. This study suggests a biological Trichoderma-based protective layer that may have significant value in mild cases of LWD.