A synthesis route to access substituted triazole-pyrazole hybrids from triazenopyrazoles has been established and applied to obtain a library of over 50 novel triazole-pyrazole hybrids. The selective N-functionalization of the triazene-protected pyrazoles was conducted, and the cleavage of triazenopyrazoles to the corresponding azides was described for the first time with regioisomer 17, whereas regioisomer 18 is acid-insensitive and cannot be converted. The azides were reacted to the respective triazole product in a CuAAC reaction; this step could also successfully be conducted in a sequential one-pot approach from the triazenopyrazole precursor. The developed protocol was adapted for solid-phase synthesis to demonstrate the applicability of triazenoyprazoles as immobilized building blocks.