Class II malocclusion is one of the most common dental anomalies and the use of intermaxillary elastomers is the standard method in its treatment. However, orthodontic elastics cannot exert continuous force over a period of time due to force degradation. Our goal was to mechanically characterize the different types of elastomers during static and cyclic loads, based on uniform methodology and examine the morphological changes after loading. Ten types of latex-containing and four latex-free intermaxillary elastics were examined from six different manufacturers. To determine the mechanical characteristics of the elastomers, tensile tests, cyclical tensile fatigue tests and 24 h relaxation tests were performed, and the elastics were also subjected to scanning electron microscopy (SEM) and Raman spectroscopy. Regardless of the manufacturer, the latex-containing elastomers did not show significant differences in the percentage of elongation at break during the tensile test. Only one type of latex-containing elastomer did not tear during the 24 h cyclical fatigue test. Fatigue was confirmed by electron microscopy images, and the pulling force reduced significantly. During the force relaxation test, only one latex-free ligature was torn; the force degradation was between 7.8% and 20.3% for latex ligatures and between 29.6% and 40.1% for latex-free elastomers. The results showed that dynamic loading was more damaging to ligatures than static loading, latex-containing elastomers were more resistant than latex-free elastics, and which observation could have clinical consequences or a potential effect on patient outcome.