This study presents a newly developed timber–glass point connection intended to strengthen existing timber elements in a reversible and visually unobtrusive manner. The new connection consists of an aluminium insertion, two-component structural bonding epoxy resin adhesive, and self-tapping screws. The connection offers the possibility of easy attachment and detachment of the glass element from the strengthened timber element. Seven timber–glass specimens were constructed to perform an experimental investigation of the shear load-bearing capacity and load-slip behaviour of the connection. The aluminium insertion is bonded to a tempered glass strip with a hole and is screwed to the spruce timber block. The timber–glass connection preparation process is thoroughly presented. A special testing apparatus was developed to perform the experiments on a hydraulic universal testing machine. The experimental results are evaluated using analytical expressions and a finite-element simulation. The average connection load-bearing capacity obtained from the experiments of the analysed specimen was 13.31 kN, and the average slip modulus was 20.48 kN/mm. All connections failed on account of self-tapping screw failure, whereas the tempered glass strips remained undamaged.