From 1 to 100, the digit 9 appears 20 times: 9, 19, 29, 39, 49, 59, 69, 79, 89 (9 times in the units place), and 90, 91, 92, 93, 94, 95, 96, 97, 98, 99 (10 times in the tens place, with 99 having one more in the units place, totaling 11, but wait - 99 counts twice. Let me recount: 9, 19, 29, 39, 49, 59, 69, 79, 89 = 9 occurrences. Then 90, 91, 92, 93, 94, 95, 96, 97, 98, 99 = 10 occurrences in the tens place. But 99 also has a 9 in the units place. So total = 9 + 10 + 1 = 20.