This attempt covers an investigation of cutting temperature at interfaces of Fiber Metal Laminates (FMLs) made of glass fiber-reinforced polymer (GFRP) stacked with an Al2020 alloy. GFRP/Al/GFRP and Al/GFRP/Al composite stacks are both investigated to highlight the effect of stacking arrangement on thermal behavior within the interfaces. In a first test series, temperature history is recorded within the metal/composite stack interfaces using preinstalled thermocouples. In a second test series, a wireless telemetry system connected to K-type thermocouples implanted adjacent to the cutting edge of the solid carbide drill is used to record temperature evolution at the tool tip. Focus is put on the effects of cutting speed and stacking arrangement on the thrust force, drilling temperature, and delamination. From findings, the temperature histories show high sensitivity to the cutting speed. When cutting Al/GFRP/Al, the peak temperature is found to be much higher than that recorded in GFRP/Al/GFRP and exceeds the glass transition point of the GFRP matrix under critical cutting speeds. However, thrust force obtained at constitutive phases exhibits close magnitude when the stacking arrangement varies, regardless of cutting speed. Damage analysis is also discussed through the delamination factor at different stages of FML thickness.