This paper reports the synthesis of oligomeric dispersed dyes based on α-naphthol-formaldehyde (NF) oligomer by coupling of various diazonium salt to α-NF oligomer. α-NF oligomer was prepared by the condensation of a-naphthol with formaldehyde in presence of oxalic acid. To achieve suitable oligomer in the present study, several variables namely molar ratios of reactants, temperature, time and catalyst have been optimized in the synthesis. A series of oligomeric azo dyes have been prepared by coupling various diazonium salts of aromatic amines to α-NF oligomer. Their dyeing on polyester, nylon and wool resulted in attractive hues an fibres. In this study of oligomeric azo-NF dyes the dyeing of the fibres completed in short time and most important is that no patches were observed on the fibres, while earlier reported oligomeric dyes form patches on the fibre. They were characterized in terms of their softening points, yield, colour, solubility and UV-visible spectra. Structure-property relationships are discussed and dyeing on polyester (PET), nylon-6, 6 and wool are assessed to have excellent fastness properties.