Masters where he won his first round match but lost in the second round to 14th seed MaliVai Washington in three sets. After playing in New Haven where he lost to world No. 8 and eventual champion Boris Becker, he qualified for the US Open in what would be the best result of his career. He won the first and second rounds to play the defending champion and world No. 1 Pete Sampras in the third round. He surprisingly won the opening set but lost the next three set to lose the match 6–4, 2–6, 4–6, 3–6. Smith would finish the rest of the year by playing in more challenger events with his best result coming at his last tournament of the year at the Sao Luis Challenger where he made the final but lost in three sets. He also made the finals of the doubles draw partnering João Cunha e Silva and won in three sets which would be his best doubles result of the year. 1995–2002 1995 saw a severe dip in form and rankings for Smith in both singles and doubles. His singles ranking dropped from 161 at the beginning of the year to 743 at the end of the year and he failed to make one challenger final in both singles and doubles. In 1996, Smith won his third and last doubles title at the Shanghai Open once again partnering fellow Bahamian Mark Knowles where they beat 2nd seed Jim Grabb and Michael Tebbutt in the final in three sets. In doubles that year, he would also make the third round of the US Open partnering Shelby Cannon and win the last challenger title of his career at the Tanagura Challenger. In 1997, Smith played both his last singles and doubles ATP tournaments. His last singles came at the Japan Open after he qualified for the main draw but lost in the first round to fellow qualifier Olivier Delaître in three sets. His last doubles match came after he played in a few more ATP doubles tournaments in 1997 including the US Open, his last grand slam, and the Presidents Cup where he and German Karsten Braasch made the semifinals as the top seed. He played his last ATP doubles tournament and ATP tournament in both singles and doubles at the Romanian Open where he partnered Jeff Tarango and lost in the first round to Luis