Background: Although handcrafted radiomics features (RF) are commonly extracted via radiomics software, employing deep features (DF) extracted from deep learning (DL) algorithms merits significant investigation. Moreover, a “tensor’’ radiomics paradigm where various flavours of a given feature are generated and explored can provide added value. We aimed to employ conventional and tensor DFs, and compare their outcome prediction performance to conventional and tensor RFs. Methods: 408 patients with head and neck cancer were selected from TCIA. PET images were first registered to CT, enhanced, normalized, and cropped. We employed 15 image-level fusion techniques (e.g., dual tree complex wavelet transform (DTCWT)) to combine PET and CT images. Subsequently, 215 RFs were extracted from each tumor in 17 images (or flavours) including CT only, PET only, and 15 fused PET-CT images through the standardized-SERA radiomics software. Furthermore, a 3 dimensional autoencoder was used to extract DFs. To predict the binary progression-free-survival-outcome, first, an end-to-end CNN algorithm was employed. Subsequently, we applied conventional and tensor DFs vs. RFs as extracted from each image to three sole classifiers, namely multilayer perceptron (MLP), random-forest, and logistic regression (LR), linked with dimension reduction algorithms. Results: DTCWT fusion linked with CNN resulted in accuracies of 75.6 ± 7.0% and 63.4 ± 6.7% in five-fold cross-validation and external-nested-testing, respectively. For the tensor RF-framework, polynomial transform algorithms + analysis of variance feature selector (ANOVA) + LR enabled 76.67 ± 3.3% and 70.6 ± 6.7% in the mentioned tests. For the tensor DF framework, PCA + ANOVA + MLP arrived at 87.0 ± 3.5% and 85.3 ± 5.2% in both tests. Conclusions: This study showed that tensor DF combined with proper machine learning approaches enhanced survival prediction performance compared to conventional DF, tensor and conventional RF, and end-to-end CNN frameworks.