(1) Background: Transvenous lead extraction (TLE) can become far more complex when unanticipated difficulties arise. The aim was to develop a simple scoring system that allows for the prediction of the difficulty and complexity of this significant procedure. (2) Methods: Based on analysis of 3741 TLE procedures with and without complicating factors (extended fluoroscopy time, need for second-line instruments, and advanced techniques and instruments), a five-point Complex Indicator of Difficulty of (TLE) Procedure (CID-TLEP) scale was developed. Two or more points on the CID-TLEP scale indicate a higher level of procedure complexity. (3) Results: Patient age below 51 years at first CIED implantation, number of abandoned leads, number of previous procedures, passive fixation and multiple leads to be extracted, and a ratio of dwell time of oldest lead to patient age during TLE of >0.13 are significant predictors of higher levels of lead extraction complexity. The ROC analysis demonstrates that a point total (being the sum of the odds ratios of the above variables) of >9.697 indicates a 21.83% higher probability of complex TLE (sensitivity 74.08%, specificity 74.46%). Finally, a logistic function was calculated, and we constructed a simple equation for lead extraction complexity that can predict the probability of a difficult procedure. The risk of complex extraction (as a percentage) is calculated as [1/(1 + 55.34 · 0.754X)] · 100 (p < 0.001). (4) Conclusion: The LECOM score can effectively predict the risk of a difficult transvenous lead extraction procedure, and predicting the probability of a more complex procedure may help clinicians in planning lead removal and improving patient management.