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Mycotoxins should be monitored in order to properly evaluate corn silage safety quality. In the present study, corn silage samples (n = 115) were collected in a survey, characterized for concentrations of mycotoxins, and scanned by a NIR spectrometer. Random Forest classification models for NIR calibration were developed by applying different cut-offs to classify samples for concentration (i.e., μg/kg dry matter) or count (i.e., n) of (i) total detectable mycotoxins; (ii) regulated and emerging <i>Fusarium</i> toxins; (iii) emerging <i>Fusarium</i> toxins; (iv) <i>Fumonisins</i> and their metabolites; and (v) <i>Penicillium</i> toxins. An over- and under-sampling re-balancing technique was applied and performed 100 times. The best predictive model for total sum and count (i.e., accuracy mean ± standard deviation) was obtained by applying cut-offs of 10,000 µg/kg DM (i.e., 96.0 ± 2.7%) or 34 (i.e., 97.1 ± 1.8%), respectively. Regulated and emerging <i>Fusarium</i> mycotoxins achieved accuracies slightly less than 90%. For the <i>Penicillium</i> mycotoxin contamination category, an accuracy of 95.1 ± 2.8% was obtained by using a cut-off limit of 350 µg/kg DM as a total sum or 98.6 ± 1.3% for a cut-off limit of five as mycotoxin count. In conclusion, this work was a preliminary study to discriminate corn silage for high or low mycotoxin contamination by using NIR spectroscopy.