Rasgulla, the popular Indian dairy-based dessert, was fortified by using pineapple to improve its nutritional and different physical parameters like color, texture and sensory attributes. Being a highly nutritious, palatable fruit with excellent flavor and visual color characteristics, pineapple fortification provides an edge over normal dairy rasgulla. Comparative analysis of nutritional, X-ray diffraction, texture and sensory characteristics for normal rasgulla sample and pineapple with different drying process (pulp (PP), convective (PH), microwave (PMW), microwave convective (PMWC), and freeze-dried (PF)) fortified rasgulla samples were done. PH was found with maximum carbohydrate (40.60±2.04) and minimum protein content (5.91±0.95). PMWC was found with the maximum total color difference (ΔE = 48.79±3.33). Pineapple fortification did not alter the crystal characteristics of the rasgulla samples. Normal rasgulla showed the lowest hardness value while PMWC was the hardest one. The results obtained from the analysis were further comparatively segregated with the help of principal component analysis, hierarchical cluster analysis and self-organizing map to optimize the analysis frequency towards a more accurate result. It was found that more or less the same trends in results were obtained by all three analysis tools. It can be concluded that machine learning-based self-organizing map can be more sophistically used for classification between different parameters even in case of complex non-linear problems also. Among the entire samples microwave, convective dried pineapple rasgullawas found to be the best in terms of all the observed parameters.