Abstract Background Low back pain (LBP) is a burdensome problem affecting amateur cyclists. This cross-sectional study analysed Italian amateur cycling cohort’s demographic and sport-specific characteristics, the prevalence and characteristics of LBP among this population, its possible association factors, the management strategies adopted to deal with LBP and the sample’s beliefs among possible LBP triggers. A web-based cross-sectional survey was created. The questionnaire included 56 questions divided into six sections, querying the sample’s demographic, clinical, and cycling characteristics. Binomial logistic regression with a Wald backward method was performed to ascertain the effects of some covariates (“Sex”, “Age”, “Body Mass Index”, “Sleep hours”, “Work type”, “Cycling year”, “Number of training sessions per week”, “Stretching sessions”, “Being supervised by a coach or following a scheduled training”, “Other sports practised regularly”, “Number of cycling competitions per year”, “Past biomechanic visits”, “Specific pedal training”, “LBP before cycling”) on the likelihood of developing LBP in the last 12 months. Results A total of 1274 amateur cyclists answered the survey. The prevalence of LBP appeared to be 55.1%, 26.5% and 10.8% in life, in the last 12 months and the last 4 weeks, respectively. The final model of the logistic regression included the covariates “Sex”, “Work type”, “Cycling year”, “Being supervised by a coach or following a scheduled training”, “Other sports practised regularly”, “Specific pedal training”, “LBP before cycling”, among which “Cycling year” (variable “Between 2 and 5 years” vs. “Less than 2 years”, OR 0.48, 95% CI [0.26–0.89]), “Being supervised by a coach or following a scheduled training” (OR 0.53, 95% CI [0.37–0.74]), “Specific pedal training” (OR 0.69, 95% CI [0.51–0.94]), and “LBP before cycling” (OR 4.2, 95% CI [3.21–5.40]) were found to be significant. Conclusions The prevalence of LBP among Italian amateur cyclists seems to be less frequent compared to the general population. Moreover, undergoing previous specific pedal training and being supervised by a coach or following scheduled training drew a negative association with LBP development. This evidence highlights the importance of being overseen by specific sport figures that could offer a tailored evidence-based training to reach good physical level and to practise sports safely.