Background: Chest tube malfunction, after the tube thoracostomy, is often the result of an inappropriate chest tube tip position. The aim of this study was to analyse the precision of chest tube placement using the targeted wire guide technique (TWG technique) with curve dilator and to compare it to the classical surgical technique (CS technique). Materials and methods: In this clinical study 80 patients with an indication for thoracic drainage, due to pneumothorax or pleural effusion were included. Experimental group contained 39 patients whose chest tube was placed using the TWG technique. The control group contained 41 patients whose chest tube was placed using the CS technique. Results: The comparison of the outcomes of the two techniques applied suggests that the TWG technique was significantly more successful in achieving adequate (precise) chest tube placement, irrespective of patient diagnosis (TWG vs. CS in all patients, 78.4% vs. 36.6%, p < 0.001). In the pleural effusion group, TWG and CS had success rates of 78.2% and 37.5% (p = 0.005), respectively, while in pneumothorax group, TWG and CS had success rates of 78.6% and 35.3% (p = 0.029), respectively. Conclusions: Using a curved dilator and the TWG technique for the thoracic drainage procedure we found statistically significant advantage to the TWG technique in comparison to the CS technique (78% vs. 37%) regarding precise chest tube placement within the pleural cavity. Introducing the materials and technique used in this clinical trial into clinical practice may improve the quality of thoracic drainage, including residual volume of air and/or fluid, poor functioning of the chest tube, and, as a consequence of both, prolonged hospitalisation.