The 1939 Portsmouth Trojans made the first appearance for a Trojan basketball team in the state tournament since the 1934 team finished state runnerup to Dayton Roosevelt. PHS opened the season with wins over Columbus South, Marietta, and Norwood. Akron North handed the Trojans their first defeat of the season, and the Hamilton Big Blue followed that with a win over the Men Of Troy. Hamilton would beat PHS again later in the season. Springfield was beaten twice, as was Chillicothe and Ironton. Huntington swept two from Portsmouth, while Middletown would gain a split later in the season.

The 1941 Portsmouth Trojans had the distinction of being the 8th PHS basketball team to qualify for the state tournament, which at that time was formatted in a Sweet 16 bracket. In the regular season, the Trojans beat Marietta, to open the 1940-41 campaign, then followed with a 38-22 win over Akron North. Dayton Roosevelt, which defeated PHS in the 1934 state championship game, fell to the Men Of Troy by a 40-23 count (Del Rice 18 points). Sciotoville, Chillicothe, and Ironton all ended up on the short end of the scoreboard, all by lopsided margins.

The 1948 Portsmouth Trojans (17-6) won the district championship, which was only the second one of the decade of the 40's (1941 the other). PHS had a 3-4 record in the GOL, beating Hamilton, Springfield, and Lima once, while losing to Middletown twice. In the regular season, the Trojans won 2 games by 1 point, and 2 games by 2 points. Portsmouth swept Chillicothe, split with Ironton, and beat Columbus West, Greenfield, Washington CH, Huntington East WV, Monroe, Lima South.

The 1950 Portsmouth Trojans won the school's first of 6 district titles in the 1950's, and a player with one of the most colorful names in Trojan history would make a key play vs. Lancaster in the district semifinal. James "Sweetwater" Douglas made a steal and basket to clinch a 49-48 win over the Golden Gales. Portsmouth would beat Chillicothe 51-49 to win the district championship. 

The 1951 Portsmouth Trojans went 18-4, and won a memorable showdown with the Chillicothe Cavaliers in the district championship. CHS had come into the game with a perfect 20-0 mark, and had their sights set on making the state tournament. But the Men of Troy had plans to end the Cavaliers hopes, and that they did with a late rally to sqeeze by the Ross Countians by a 53-51 score.

The 1952 Portsmouth Trojans posted a mark of 14-8 for the regular season, and with it was the 3rd consecutive district championship. The Trojans had a rough year in the tough Greater Ohio League, failing to win a game as they went 0-6. The GOL proved how tough it was because PHS went 14-2 in all the other games, and Middletown won the state championship, giving the GOL its 6th state title since 1944.

The 1954 Portsmouth Trojans district championship team was the school's 4th in 5 years. Despite going 9-9 in the regular season, the Trojans still had some commendable wins along the way. PHS crushed Cincinnati Roger Bacon, Cincinnati Elder, and Cincinnati Walnut Hills. The Trojans beat Ironton twice, beat Columbus East, nipped Springfield 71-70, and handled Lima easily 78-60. Portsmouth then pulled off a big upset to end the regular season, as state ranked Dayton Stivers fell to the Trojans 81-52. Leroy Carr was the leading scorer on this team, and had games of 35, 33, and 32 points.

The 1955 Portsmouth Trojans not only won the school's 5th district title in 6 years, but at one point of the season they were ranked #1 in the AP Poll. PHS had an outstanding record of 20-4, only the 4th time in school history that a Trojan basketball team had won 20 games. In addition, it was the first time in Portsmouth's GOL history that the Trojans swept Middletown, Hamilton, and Springfield twice each. The only league losses that year were to Lima and Mansfield (Mansfield was a member of the GOL at that time). The only other loss in the regular season was to Columbus East.

The 1956 Portsmouth Trojans' district championship was the school's 6th in 7 years. PHS compiled a record of 16-7, with a 5-5 mark in the Greater Ohio League (at that time Mansfield was a member of the GOL). In the regular season, Portsmouth gave a double whipping of Ironton, beat Cincinnati Western Hills and Cincinnati Hughes, and also topped Columbus East. The win over Hughes was a nice way to start out the season considering that the Big Red had eliminated the Trojans in the regional final the year before.

After coming off 3 straight losing seasons for the first time in school history, the 1960 Portsmouth Trojans brought the basketball program back to prominence with an 18-5 season, winning a district title. The Trojans secured their first opening Greater Ohio League win in 4 years with a 64-40 triumph over Hamilton Taft. Portsmouth finished a very respectable 6-4 in the GOL, with a sweep of Middletown 68-58 and 62-52, and Hamilton Taft. The sweep of Middletown was particularly sweet in that the Middies had beaten the Trojans 9 straight times.