Since the OHSAA began a statewide tournament in 1923, there have been many changes in the number of classes since that time. From 1923-1971, there were only 2 classes of basketball teams in Ohio. Portsmouth was a member of the larger class of schools during this time period. Around 1950, there were about 1,150 schools total in Ohio, which meant that advancing to the state tournament was even more difficult than it is today. Still, the Trojans captured state championships in the larger class in 1931 and 1961, and made state appearances in 1925, 1926, 1927, 1929, 1934, 1939, and 1941. In 1971, the OHSAA decided to go to a three class system known as Class AAA, AA, and A. Portsmouth was still in the largest class of schools from 1971 until 1977. Chillicothe handed PHS its first loss in the Class AAA tournament, as the Trojans were defeated in the sectional. In 1972, Portsmouth captured its only Class AAA district title, besting Zanesville 52-46. PHS went on to lose to #1 Celina in the Class AAA regionals at the Fairgrounds Coliseum 77-71 in OT despite Mike Lovenguth's 36 points. The Trojans advanced to the district finals in Class AAA in 1975, losing to Zanesville 67-51. Portsmouth's last game in Class AAA came in the 1977 sectional tournament at Ohio University, as Miami Trace ended the Trojans season with a 73-68 victory. In 1978, Portsmouth dropped to Class AA and once again made its name known statewide, as the Trojans won the state championship with a 63-62 thriller over Cleveland Cathedral Latin. Portsmouth remained in Class AA from 1978-1987, then the OHSAA expanded once again into a 4 divisions. The Trojans won Class AA district titles in 1978, 1980, 1982, 1983, and 1987.
Portsmouth High School made history in the very first year of the new four division setup in 1988 as the Trojans won the D2 state championship with a 54-47 win over Chesterland West Geauga. PHS ended that season with a 27-1 record which to this day is the best in school history. Two years later saw PHS once again challenge for a state title, but this time the Trojans came up short to Dayton Colonel White 71-57 in the D2 state championship. The Trojans won district titles in Division 2 in 1988, 1989, 1990, 1991, 1994, 1999, and 2001. Portsmouth continued to be a Division 2 school until 2002, when enrollment figures dropped PHS to Division 3 for the first time. The Trojans advanced to the district final in 2002, where Eastern Brown ended the Men of Troy's season with a 66-48 win. In 2003, Portsmouth went back to D2 status and lost in the sectional final to Gallia Academy 53-51 on a buzzer beater by Donnie Johnson of GAHS. Due to changing enrollments on a yearly basis, Portsmouth went back to Division 3 in 2004 and has stayed there ever since. The Trojans made history yet again by going to the D3 state tournament in 2011 and 2012, with those back to back appearances being a first in school history. Those two appearances pushed PHS into second place all-time for most state appearances with 15.
No matter what class Portsmouth High School has been a member of, it has made notoriety in each class. The Trojans have had remarkable success at every level, and whether is has been competing against over 500 schools or 200, whether it be 2, 3, or 4 classes, PHS has made its name as one of the elite basketball programs in Ohio all-time.