Most passerines have a repertoire of different song patterns, and a repertoire size is thought to signal aspects of male quality. We investigated the relationship between advertising song features (including their time and frequency characteristics), male age (yearlings or older) and reproductive success (successful or unsuccessful) in Whinchat Saxicola rubetra population in abandoned fields of Vologda region, Russia. We estimated minimum and maximum song frequencies, song length and pauses between them and the repertoire size of Whinchat males with the identified age and type of reproductive success. No significant differences in the time and frequency characteristics of vocalization of yearlings and older males as well as the successful and unsuccessful males were discovered. We concluded that Whinchat is a species with rather a rich song repertoire. A total of 218 song types were singled out in the song repertoires of thirty-five males and about 22 song types were found in their individual repertoires. The repertoire size of adult males significantly exceeds the repertoire size of the yearlings. There are no significant differences in the repertoire size among Whinchats with different reproductive success. Our scientific research was sponsored by the Russian Foundation for Basic Research (RFBR) (13-04-00745-a).