Not much time to post now or for the next few days, but to tide you over, here's some video that purports to be from an IU-Michigan game from 1957. For the record, IU lost 27-13, in the second to last game of a 1-8 season. IU beat Villanova, and sadly, the 14 point loss in Ann Arbor was IU's most competitive loss. Michigan was 5-3-1 and in the midst of a two decade slump (by Michigan standards) between the tenures of Fritz Crisler and Bo Schembechler. As the video shows, there were lots of empty seats in AA that day.
That loss did come in the midst of what has been the only competitive stretch in the IU-Michigan series. From 1954 through 1967, IU went 4-4 against Michigan even though only one of the eight games was in Bloomington. From 1968 to present, IU is 1-30 against U-M.