Adhesives that involve adhesion to the skin have been of great technological importance in medical or pharmaceutical fields, including recently emerging wearable sensors and electronics. The objective of this work was to evaluate the performances of silicone-based adhesives with skin, using a peel adhesion test. Specifically, we explored the effect of adhesive cleansing, which is an inevitable daily event for patients' comfort in long-term applications. Firstly, three medical grade silicone gels, Silbione® RT 4717, Silbione® RT 4642, and Silpuran® 2130, were used to fabricate adhesive pads. Their peel strength values were subsequently measured and compared, among which Silbione® RT gel 4717 possessed the highest peel strength. Therefore, it was selected as the raw material to fabricate the pads with a thickness range of 640-740 μm. Secondly, the peel adhesion of Silbione® RT 4717 adhesive pad was further compared with a series of commercial products that employ various medical-grade adhesives. The peel strength results indicated that our custom-made adhesive pad had an adequately strong adhesion for clinical use. Thirdly, in order to observe and predict the long-term performance of the adhesives, an aging test was performed in an ambient environment, revealing that Silbione® RT 4717 adhesive remained highly sticky for 5 days. Lastly, adequate cleansing protocols were established by monitoring the changes in peel strength after washing and wiping events. The reusability analysis showed that Silbione® 4717 adhesive pad was reusable in a one-week period for the washing method and 3 days for the wiping method.