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.

Roster: B. Smith, K. Booker, J. Young, D. Gambill, Jerry Barry, E. Dupuy, D. Anderson, D. Leightenheimer, E. Sparks, D. Triggs, Fred Shumate

Coach: Bill Rohr

Regular Season:

PHS 39, Portsmouth East 25

PHS 44, Columbus West 43

PHS 46, Chillicothe 31

PHS 44, Greenfield 40

PHS 37, Hamilton 35

PHS 44, Washington CH 43

PHS 46, Huntington East WV 44

Springfield 52, PHS 42

Ironton 48, PHS 40

Middletown 45, PHS 38

PHS 71, Chillicothe 53

PHS 46, Lima South 24 

Roster: Don Ellis, James Douglas, B. Doll, Bert Barney, B. Kimble, P. Newman, D. Frecka, B. Armstrong, C .Howell, B. Ison, J. Appel, G. Hatch

Coach: Bill Rohr

Regular Season:

PHS 62, Portsmouth East 28

PHS 58, Hillsboro 22

PHS 51, Ironton 40

PHS 48, Greenfield 40

Hamilton 47, PHS 44

PHS 58, Columbus East 37

PHS 58, Huntington East WV 34

PHS 43, Springfield 37

PHS 52, Middletown 47 

Chillicothe 55, PHS 52

PHS 55, Cincinnati Elder 34

PHS 56, Springfield 50

Roster: Bill Ison, Don Ellis, Dick Klitch, Dick Frecka, Thom Gentry, Bob Armstrong, Carroll Howell, Wayne Cooper, Greg Hatch, John Vournazos, Theron White

Coach: Bill Rohr

Regular Season:

PHS 71, Portsmouth East 50

PHS 55, Cincinnati Walnut Hills 29

PHS 61, Ironton 33

PHS 78, Columbus Aquinas 27

PHS 53, Hamilton 51

PHS 57, Circleville 28

PHS 67, Huntington East WV 49

PHS 56, Springfield 40

Middletown 58, PHS 52

PHS 71, Cincinnati Elder 34

PHS 47, Columbus East 41

Roster: Dave Dever, Tom Quinn, Bill Armstrong, Thom Gentry, Sonny White, Leroy Carr, John Vournazos, Dave Arnold, Jack Doll, Ted Hacquard, Bill Oppenheimer, Buddy Oakley, Theron White

Coach: George Heller

Regular Season:

PHS 59, Marietta 52

Cincinnati Walnut Hills 47,  PHS 45

PHS 66, Columbus Aquinas 39

Hamilton 66, PHS 32

PHS 57, Dayton Roosevelt 45

PHS 48, Huntington East WV 42

Springfield 59, PHS 43

Middletown 62, PHS 56

PHS 64, Ironton 53

PHS 63, Columbus Central 51

Roster: Jerry Higgins, Duck Frazier, Bob Parlin, Mike Swearingen, Leo Brown, Leroy Carr, Bill Clifford, Mick Grooms, Curt Gentry, Milt Parker

Coach: George Heller

Regular Season: 

PHS 73, Cincinnati Walnut Hills 52

Ashland KY 67, PHS 55

Hamilton 63, PHS 42

PHS 90, Cincinnati Elder 38

Columbus Central 50, PHS 42

Springfield 69, PHS 64

Middletown 77, PHS 65

PHS 80, Cincinnati Roger Bacon 57

PHS 82, Ironton 57

PHS 64, Columbus East 59

PHS 71, Springfield 70

Roster: Curt Gentry, Milt Parker, Bill Clifford, Jerry Higgins, Duck Frazier, Bruce Johnson, Jerry Copley, Jim Duncan, Chet Corbitt, Mike Williams, Bill Spinks, Larry Sunafrank

Coach: George Heller

Regular Season:

PHS 68, Greenfield 46

PHS 78, Ashland KY 46

PHS 79, Hamilton 53

PHS 54, Dayton Dunbar 43

PHS 73, Lancaster 62

PHS 65, Springfield 49

PHS 81, Middletown 60

PHS 64, Cincinnati Roger Bacon 37

PHS 62, Ironton 53

Columbus East 60, PHS 56

PHS 56, Middletown 41

Roster: Tony Price, Bruce Johnson, Jerry Hughes, Don Frazier, Ron Shumate, Mike Williams, Al White, Dave Otworth, Larry Sunafrank, Bill Spinks

Coach: George Heller

Regular Season:

PHS 52, Cincinnati Hughes 51

Columbus Central 68, PHS 57

PHS 50, Springfield 40

PHS 61, Ironton 46

Middletown 75, PHS 62

PHS 67, Lancaster 62

Hamilton 87, PHS 83

PHS 58, Columbus East 50

Mansfield 60, PHS 58

PHS 75, Lima 56

Springfield 73, PHS 72

Middletown 85, PHS 71

Roster: Corky Burgess, Harry Roark, Rudy Shively, Ken Nagle, C.A.Hartley, Dave Colgrove, Jim Fuller, Dick Spencer, John Adams, Buck Copley, Mike Haley

Regular Season: 

PHS 74, Cincinnati Western Hills 59

PHS 76, Lima 52

PHS 70, Ironton 58

PHS 60, Hamilton Garfield 48

Springfield 73, PHS 64

Lima 61, PHS 50

PHS 70,  Ironton 50

PHS 65, Middletown 58

Hamilton Garfield 66, PHS 55

PHS 83, Ashland 42

PHS 92, Portsmouth East 36

PHS 75, Cincinnati Aquinas 49

PHS 86, Lancaster 62