In field ecological and behavioural studies, it is often necessary to identify specific individuals. In birds, colour rings are frequently used to mark individuals; however, rings are often difficult to observe, especially in small species and dense habitats. Acoustic-based monitoring detecting individuals by their characteristic vocalization is a potentially suitable alternative, but this approach is challenging in species with complex songs. On the example of the Tree Pipit (Anthus trivialis), a small migratory passerine often singing in flight or from perches obscured by foliage, we demonstrate that acoustic monitoring based on the syllable repertoire can be very efficient tool for individual recognition. During a 3-year study, we obtained over 500 recordings from males from one study population (a number of them returning after winter). Males banded with colour rings were repeatedly recorded throughout the seasons, and syllable repertoires were determined from spectrograms for each recording. The repertoire of each unambiguously identified male was distinct and stable within as well as between seasons; and males with similar syllable repertoires differed in syntax. Based on the congruence between identification based solely on spectrogram assessment, and that based on observation of colour rings, we inferred that reliable identification of singing males (including non-ringed ones) was possible in the studied population from assessing a repertoire and song syntax of <5-min recording (containing 20–30 songs). The acoustic-based data: (i) increased the overall estimated number of territorial males at the study locality (from 49 ringed to 61), and improved the estimates of the period of their presence; (ii) revealed dynamic within-season changes in territory occupancy that would otherwise be missed; and (iii) allowed identification of returning birds (including non-ringed ones and those actively avoiding approaching humans). Our results suggest that some commonly used methods may substantially underestimate return rates of migratory bird species. Individual acoustic monitoring should be applicable on various bird species with complex song and stable repertoires, and may be particularly useful for those living in dense habitat or sensitive to handling.