Microdeep drawing has great potential in microsystem technologies, electron industries, new energy, etc. Microsquare cups with internal side length of 1 mm were formed in this study. The blank material was pure copper C1100 with a thickness of 50 μm which was annealed in vacuum condition at 573 and 723 K for 1 h, respectively. The experiments were conducted with an electronic universal testing machine. Three kinds of different lubrication conditions and blank holder force (BHF) were used, and the experimental velocity was 0.05 mm/s. The results showed that a microsquare cup with a limiting drawing ratio (LDR) of 1.89 was well formed. Compared to the as-received blank, the annealed blank decreased the drawing force and the earings and increased the LDR. The polyethylene (PE) film, which decreased the drawing force and increased the LDR, was much better than other lubrication conditions. The wrinkles decreased with the increase of the BHF under a specific value.