In numerous studies of the outer Galactic halo some evidence for accretion has been found. If the outer halo did form in part or wholly through merger events, we might expect to find coherent streams of stars and globular clusters following orbits similar to those of their parent objects, which are assumed to be present or former Milky Way dwarf satellite galaxies. We present a study of this phenomenon by assessing the likelihood of potential descendant "dynamical families" in the outer halo. We conduct two analyses: one that involves a statistical analysis of the spatial distribution of all known Galactic dwarf satellite galaxies (DSGs) and globular clusters, and a second, more specific analysis of those globular clusters and DSGs for which full phase space dynamical data exist. In both cases our methodology is appropriate only to members of descendant dynamical families that retain nearly aligned orbital poles today. Since the Sagittarius dwarf (Sgr) is considered a paradigm for the type of merger/tidal interaction event for which we are searching, we also undertake a case study of the Sgr system and identify several globular clusters that may be members of its extended dynamical family. In our first analysis, the distribution of possible orbital poles for the entire sample of outer (Rgc > 8 kpc) halo globular clusters is tested for statistically significant associations among globular clusters and DSGs. Our methodology for identifying possible associations is similar to that used by Lynden-Bell & Lynden-Bell, but we put the associations on a more statistical foundation. Moreover, we study the degree of possible dynamical clustering among various interesting ensembles of globular clusters and satellite galaxies. Among the ensembles studied, we find the globular cluster subpopulation with the highest statistical likelihood of association with one or more of the Galactic DSGs to be the distant, outer halo (Rgc > 25 kpc), second-parameter globular clusters. The results of our orbital pole analysis are supported by the great circle cell count methodology of Johnston, Hernquist, & Bolte. The space motions of the clusters Pal 4, NGC 6229, NGC 7006, and Pyxis are predicted to be among those most likely to show the clusters to be following stream orbits, since these clusters are responsible for the majority of the statistical significance of the association between outer halo, second-parameter globular clusters and the Milky Way DSGs. In our second analysis, we study the orbits of the 41 globular clusters and six Milky Way-bound DSGs having measured proper motions to look for objects with both coplanar orbits and similar angular momenta. Unfortunately, the majority of globular clusters with measured proper motions are inner halo clusters that are less likely to retain memory of their original orbit. Although four potential globular cluster/DSG associations are found, we believe three of these associations involving inner halo clusters to be coincidental. While the present sample of objects with complete dynamical data is small and does not include many of the globular clusters that are more likely to have been captured by the Milky Way, the methodology we adopt will become increasingly powerful as more proper motions are measured for distant Galactic satellites and globular clusters, and especially as results from the Space Interferometry Mission (SIM) become available.