No, a 1995 S10 2WD transmission will likely
not fit directly into a 1999 S10 2WD. While they are both S10s, there were changes made to the drivetrain between those model years. The bellhousing pattern (how the transmission bolts to the engine) and possibly the output shaft dimensions are different. Even if the bolt pattern *seems* similar, internal components and splines might not be compatible. Trying to force a mismatch could cause serious damage.
You'd need to find a transmission specifically designed for a 1999 S10 2WD.