No and no.
A tablespace is made using one or more datafiles. A datafile comes closest to a disk. The data in a tablespace is striped over the datafiles. If you delete rows from a table, there will be free space in that table. If you then shrink that table, the free space in the tablespace grows and the same in the supporting tablespaces.
If you are lucky and your table data was in the end of the datafile[s], you might be able to also shrink the datafile, after which you end up with more free space on the OS.