Things started to wobble badly around 1988, with the release of the bug-ridden PC/MS DOS 4.x and the travails of OS/2 1.x. Most people doggedly stuck to DOS 3.3 despite its limitations (particularly the max HD size of 32 MB, at a time when 40 MB disks had become commonplace).
The IBM/MS wobble couldn't have come at a worse time for DR, though. Multiuser DOS was being discontinued, and DR-DOS wasn't mature enough until version 5 (the first to include ViewMAX) - by which time Windows 3.0 had already been released.
Honestly, Microsoft were very very lucky to end up in the position they found themselves in in the early 90s. The success of Win 3 was a shock even to them, and it utterly transformed the OS market.