Previous studies of Toronto Heritage Cantonese have suggested the lack of a similar phonological contrast in English as the source of cross-linguistic influence on the phonetic production of the /y/ vs. /u/ contrast in Cantonese. By comparing both the English and Cantonese production of the same individual speakers in spontaneous speech recordings, this study addresses Chang’s (2021) call for more bilingual studies focused on individual-level cross-linguistic interactions. Results show three distinct patterns of cross-linguistic interaction: P1) three distinct vowels, P2) Cantonese /u/ merged with English /u/, and P3) Cantonese /y/ merged with English /u/. While P1 was the most frequently occurring pattern, the occurrence of P3 exclusively among second-generation speakers, among those with lower Cantonese Production Scores, and among those with the lowest Pillai Scores suggest that cross-linguistic phonetic similarity is what drives decreased acoustic distance between /y/ and /u/ rather than direct transfer of phonological categories.