A pressure regulating syringe comprises a barrel assembly terminating with a tubular tip positionable in fluid communication with a fluid chamber, a plunger that is manually and axially displaceable within a barrel of the barrel assembly, a pressure sensor mounted onto the plunger adjacent to its distal end, for generating one or more electrical signals representative of a change in pressure within the fluid chamber, circuitry housed within the plunger for processing the generated signals, and a display mounted on the plunger for displaying an output indicative of the processed signals. The output is changeable upon axial displacement of the plunger when the tubular tip is positioned in fluid communication with the fluid chamber, which is for example a cuff surrounding a medical tube. Fluid is delivered by manually manipulating a fluid delivery element in response to the displayed output until a desired fluid delivery operation is performed.