The training system Semi-Minimal-Pruned Hedge (SMPH) blends features of traditional Vertical Shoot Positioning-type (VSP) trellising systems with the concept of minimal pruning. While saving labor, this training system results in relatively high crop load and a poor leaf area to fruit weight-ratio (LFR), and thus, needs to be able to ripen grapes in a cool to moderate climate. For these reasons the impact of yield regulation strategies, including (i) shoot thinning (Darwin-Rotor), (ii) biotechnological thinning (Gibberellic acid), and (iii) bunch thinning (harvest machine) were trialed in a three year study at Geisenheim, Germany between 2017 and 2019 using Riesling (Vitis vinifera L.). The average yield per vine in SMPH (5.34 ± 1.10 kg) was 61.1% higher with a narrower LFR (14.01 cm2 g−1), compared with VSP (3.32 ± 1.02 kg, LFR: 16.99 cm2 g−1). The yield was successfully reduced and LFR simultaneously increased with shoot thinning (−33.1%, LFR: 19.04 cm2 g−1), biotechnological thinning (−18.3%, LFR: 16.69 cm2 g−1) and bunch thinning (−37.3%, LFR: 21.49 cm2 g−1). Ripening was delayed in SMPH. On average, two maturity thresholds (14.1 °Brix and 18.2 °Brix) were achieved 129 GDD (seven days according to the recorded daily mean temperatures, respectively) and 269 GDD (16 days) later in non-thinned SMPH, compared to VSP. All thinning treatments accelerated maturity progress ranging from 27 GDD (two days) to 58 GDD (three days) for 14.1 °Brix and 59 GDD (three days) to 105 GDD (six days) for 18.2 °Brix. Apart from immediate benefits on the economic efficiency, the adaption of the leaf area to fruit weight ratio using SMPH holds high potential to, (i) produce grapes targeting specific wine profiles and/or (ii) reducing the velocity of ripening under conditions of climatic change.