To investigate the effects of the properties of plastic fines on the pore water pressure generation characteristics of fine-grained soils during cyclic loadings, we used 29 sets of test data from the literature and prepared another 21 reconstituted specimens with different types of fines and fine contents (FCs) for cyclic triaxial testing. Two types of undisturbed soil specimens and three types of reconstituted soil specimens were also included for testing. The results indicated that under cyclic loading, the pore water pressure (PWP) ratios of clean sands increased slowly, stagnated, then finally accelerated until initial liquefaction, whereas those of the plastic soils containing fines with a plastic index (PI) value of >5 increased sharply in the initial stage. In addition, the cyclic stress ratio of specimens containing mudstone (PI = 12.4) and kaolinite (PI = 32.0) fines increased by 1.5–3.0 times more than non-plastic fines if the cyclic number chosen was 100. The range of the upper and lower limits of the PWP curves of the specimens with an FC of 30% were smaller that of the limits of the PWP curves of the specimens with an FC of 15%. The above results were further analyzed using a mathematical model. This paper systematically uses both the literature and laboratory test data to demonstrate that plastic fines and non-plastic fines have significantly different effects on water pressure generation under cyclic loading conditions, and a mathematical model also demonstrated the same trends. These findings are able to clarify previous unclear arguments. Thus, the model results developed in this study could also provide the field of engineering with a complete advanced calculation, requiring analysis only via software.