To address the challenges of narrow, confined spaces in traditional closed-canopy orchards, where complex terrain between and within rows hinders the operation of large and medium-sized mowers. A self-propelled intra-plant obstacle-avoiding oscillating mower was developed. Its core innovation is an integrated oscillating mechanism that achieves one-pass, full-coverage operation by coordinating a 110° fan-shaped cutting path for inter-row areas with an adaptive flipping contour-cutting action for intra-plant areas. The power and transmission systems were optimized according to the shear and bending forces of three common weed species. The integrated prototype was then built and subjected to field tests. The results showed that the shear and bending forces of all three weed species peaked at 30 mm from the root and stabilized beyond 50 mm. Field tests demonstrated a 100% intra-plant obstacle passage rate, 96.9% cutting width utilization rate, 92.07% stubble height stability coefficient, and a 1.66% missed-cutting rate, which meets the operational requirements of closed-canopy orchards.