We investigate the effect of ultrafast laser surface machining on a monocrystalline synthetic diamond sample by means of pulsed Bessel beams. We discuss the differences of the trench-like microstructures generated in various experimental conditions, by varying the beam cone angle, the energy and pulse duration, and we present a brief comparison of the results with those obtained with the same technique on a sapphire sample. In diamond, we obtain V-shaped trenches whose surface width varies with the cone angle, and which are featured by micrometer sized channels having depths in the range of 10-20 μm. By laser writing crossed trenches we are also able to create and tailor on the diamond surface pillar-like or tip-like microstructures potentially interesting for large surface functionalization, cells capturing and biosensing.