This work investigates the tribological behavior of a machined S355JR structural steel in dry sliding conditions for the development of an innovative seismic dissipation system. Flat-ended pins and disks were made of the same structural steel to simulate the conformal contact of different device parts. Pins were machined by turning, while disks were milled and turned to obtain a nominal average surface Ra roughness ranging from 0.8 µm to 6.3 µm. The influence of the surface roughness on the coefficient of friction (COF), specific wear rate (SWR), and time to steady-state (TSS) was investigated. Tribological tests were conducted reciprocating motion in dry sliding conditions to simulate the operating conditions of the device, with 1 Hz and 2 Hz reciprocating frequencies and an applied normal load of 50 N. The Rsk and Rku roughness parameters helped to better understand the tribological response of milled and turned disks, having an influence on the TSS and SWR.