Although new therapeutic strategies have emerged, survival outcomes for oral malignancies have not markedly improved, and the condition often imposes significant functional impairment. This study set out to outline the epidemiological pattern of oral cancers within a northern Italian province. Incident cases from 1996–2020 and EU-standardized rates were presented separately for Oral Cavity (OC) and OroPharyngeal (OP) cancers. Annual percent changes (APC) were quantified via joinpoint regression. Five-year survival was examined across three intervals: 1996–2000, 2001–2010, and 2011–2015. Over the 1996–2020 period, 771 oral cancer cases were identified (442 OC; 329 OP), with an age-standardized incidence of 7.28 overall (10.74 for men; 3.97 for women): 3.82 for OC and 3.47 for OP. Among males, OP incidence rose significantly until 2017 (APC 11; 95% CI 4.9–17.5) and subsequently declined; in females, the pattern remained stable. No reduction in incidence was observed for 2020 compared with 2019, despite the Covid-19 pandemic. Five-year survival for diagnoses made in 2011–2015 reached 55.6% for OC, 56.5% for OP, and 56% when combined, with slightly better outcomes for women and modest temporal variation. As of 1 January 2021, 314 individuals were living with a previous diagnosis (175 OC; 139 OP). Findings indicate an overall decrease in male cancer rates—particularly OP—and gradual long-term survival gains. Covid-19 did not adversely influence diagnosis numbers in 2020.