Research in multi-digit number comparison usually considers stimuli with the same number of digits (e.g., 3452 vs. 7831). Surprisingly, there is almost no research on the comparison of numbers that differ in length (e.g., 995 vs. 1000), which demands a focus on the number of digits in each multi-digit, despite the fact that the role of number length has been explicitly acknowledged in componential models of multi-digit processing. Our study explores whether the comparison of pairs of natural numbers that differ in length is affected by the identity of the leftmost digit of each multi-digit, and asks what is the effect of having variable proportions of trials with pairs of numbers of the same-length in the task. Across three studies participants compared numbers in blocks with different proportions of same-length multi-digit pairs (Experiment 1 and 2: 25% vs. 50% vs. 75%; Experiment 3: 0% vs. 50%). Stimuli in the different-length condition were length-digit congruent (the number with more digits starting with a larger digit: 2384 vs. 107) or length-digit incongruent (the number with more digits starting with a smaller number: 2675 vs. 398). Response times were shorter in length-digit congruent pairs than in the incongruent pairs. Unexpectedly, this effect was only slightly modulated by the proportion of same-/different-length multi-digit pairs in the experimental set. Despite its perceptual saliency, length is not the only information considered when comparing different-length numbers. The leftmost-digit is also taken into account, with variable relevance here, depending on the characteristics of the stimuli set.