Background: Undescended testis (UDT) is the most frequent pediatric anomaly of the male genitals, with a high incidence in premature male neonates. Due to the risk of long-term complications such as infertility, testicular malignancy, and psychological distress, special attention on the accuracy of management is needed. Despite the existence of well-established guidelines recommending early surgical intervention, significant delays in diagnosis, referral, and treatment are still observed in practice. Objectives: This study aims to evaluate the clinical management practices of undescended testis at a tertiary pediatric referral center over a ten-year period, with a particular focus on identifying risk factors associated with the development of postoperative testicular atrophy. Material and Methods: The following variables were extracted from patient records: the UDT location, age at surgery (we also recorded the mean age per year during the 10 years period), laterality (unilateral or bilateral), associated malformations and comorbidities, family history of UDT in first-degree relatives, type of surgical intervention (open vs. laparoscopic orchidopexy), and imaging diagnosis (ultrasonography, computer tomography). We considered testicular atrophy (TA) as negative outcome after orchidopexy. To identify the variables that independently contribute to the risk of postoperative testicular atrophy, we conducted a multivariate logistic regression analysis. Results: A total of 1082 pediatric patients UDT underwent orchidopexy between 2014 and 2023. The median age at surgery was 5.07 years, significantly exceeding current guideline recommendations. TA was observed in 24.8% of cases. Non-palpable testes, higher testicular position (particularly intra-abdominal), associated comorbidities, positive family history, and delayed surgical intervention were identified as independent risk factors for negative outcomes. The multivariate logistic regression model identified the most significant predictors of postoperative testicular atrophy as the presence of comorbidities (associated with more than an eightfold increase in risk), non-palpable testes (3.35 times higher risk compared to palpable ones), a positive family history of undescended testis (approximately 2.7 times higher risk), and older age at surgery, with each additional year of delay increasing the risk by 28.6%. Conclusions: Despite the availability of well-established guidelines, significant delays in the diagnosis and treatment of UDT persist in clinical practice. Testicular atrophy remains a relevant postoperative complication, particularly in patients with non-palpable testes, high testicular position, comorbidities, and late surgical intervention.