In recent years, the boundaries between videogaming and gambling have become increasingly blurred. In this scenario, loot boxes (LBs) may represent an activity that foster gambling behaviour because LBs are gambling-like activities embedded within videogames. Although young video gamers showed to be familiar with them, most of the studies on the relationships between LBs and gambling have been conducted with adults. To fill this gap, the aim of the present study was twofold: i) to analyze adolescents’ behaviour and severity with respect to LBs, videogaming, and gambling; ii) to develop and test a path model explaining the link between LBs use, videogaming, and gambling. We hypothesized that videogaming would mediate the relationship between LBs use and problem gambling. Participants were 1204 Italian adolescents (57% males, mean age = 15.56, SD = .57) attending high school. Results showed that 54% of them encountered at least one LB playing videogames, and 10% purchased at least one LB in the last month. Video gamers and gamblers were respectively 90% and 60%. The hypothesized path model was adequate (CFI = .994, TLI = .97, RMSEA = 0.06). In detail, LBs use had a significant and positive indirect effect on problem gambling through videogaming frequency and problem gaming. The results showed that involvement in videogaming can be taken into consideration in explaining a possible pathway from LBs to problem gambling in youth.