A series of novel mono and diazothienopyrazolone dyes were successfully synthesized and characterized, the coloration performance of the prepared dyes was assessed on wool fabrics. The structures of the synthesized dyes were characterized and confirmed by making use of IR, UV, 1HNMR and C13NMR spectrophotometers with a view to determine and confirm their chemical structure. Antimicrobial activity of the dyes fabrics has been investigated, the dyeing performance of the as prepared dyes in terms of color strength (K/S), CIE lab as well as fastness properties (washing, rubbing, perspiration and light) of the dyed wool fabrics were also investigated. The synthesized dyes exhibited high and homogeneous dyeing performance, antimicrobial activity and the fastness properties of the dyed fabrics were ranging from good to excellent.