With osmium tetroxide, no it does not appear that dihydroxylation and acetalization can be done simultaneously. Usually dihydroxylation is carried out with catalytic osmium tetroxide with a stoichiometric amount of N-methylmorpholine N-oxide (NMO). The latter regenerates the Os(VIII) species necessary to carry out the dihydroxylation and results in the formation of N-methylmorpholine, which is a weak base. Without an acid available for catalysis, the acetalization does not occur. The sequence can be accomplished in "one-pot" however. In practice, you can monitor the progress of the dihydroxylation reaction. When it is deemed complete, add catalytic acid directly to the same reaction mixture, which allows the acetal formation.
Similarly, the overall transformation has been accomplished with mCPBA, but it's not clear if happens without any further intervention. In the referenced paper below, it's not entirely clear to me when the epoxide opens, because the procedure specifies that the epoxidation step is carried out with exclusion of water. It's likely that the epoxide is stable until addition of water, which opens the epoxide to the diol and then the acetalization can occur, catalyzed by the meta-chlorobenzoic acid byproduct from the epoxidation. In some cases, they simply isolate the epoxyketone as well.