Paclitaxel (PTX) is a widely used anticancer drug but suffers from poor solubility, low oral bioavailability, and systemic toxicity. To overcome these limitations, this study investigated the use of α–α-α-cyclodextrin (α–CD) inclusion complexes incorporated into fast–dissolving microneedle patches (fast–DMNPs) composed of polyvinyl alcohol (PVA) and its blends with polyvinylpyrrolidone (PVP), hyaluronic acid (HA), or chitosan. FTIR and DSC analyses confirmed successful PTX/α–CD complexation and reduced crystallinity, while polymer blending enhanced amorphisation. Mechanical strength testing showed all formulations exceeded the minimum insertion force, though PVA/chitosan exhibited reduced insertion efficiency (69%, 84/121 needles intact). In-vitro drug release and ex-vivo permeation revealed clear differences between formulations. PVA/HA achieved the highest release (89.1% at 180 min) and permeation (2.139 ± 0.026 mg/cm2), attributed to its strong hydrophilicity and hydrogen bonding capacity. PVA–PVP provided moderate but controlled release due to crystallisation inhibition, whereas PVA–chitosan displayed limited diffusion, attributed to its rigid network and reduced needle integrity. Pure PVA showed moderate performance in both release and permeation.