Adhesion between soft matter is a universal mechanical problem in bio-engineering and bio-integration. The Johnson–Kendall–Roberts (JKR) method is widely used to measure the work of adhesion and work of separation between soft materials. In this study, the JKR theory is recaptured and three complementary dimensionless parameters are summarized to help design adhesion measurement experiments compatible with the JKR theory. The work of adhesion/separation between two commonly used soft elastomers, polydimethylsiloxane (PDMS, Sylgard® 184) and Ecoflex® 0300, is measured by the JKR method using a dynamical mechanical analyzer. Effects of base polymer to curing agent mixing ratio and solvent extraction are examined. A unified adhesion mechanism is proposed to explain the different adhesion behaviors. It is concluded that chain–matrix interaction is the most effective adhesion mechanism compared with chain–chain or matrix–matrix interactions. Chain–chain interaction obstructs chain–matrix interaction as it either blocks or entangles with surface chains which could have interacted with the matrix.