The oldest and most prestigious rowing regatta in the world, the Henley Royal Regatta began in 1839 and has been held annually since then with the exception of World Wars I and II. Henley attracts the world's top oarsmen to the Thames River in England, the races taking place in Henley which is about an hour west of London.
 
Unlike crew races in the United States, races in the Henley Royal Regatta feature only two boats per race. The winning crew moves on, while the losing crew is eliminated from the competition.
 
Penn has had the opportunity to compete in the Henley Royal Regatta 15 times—racing multiple boats in 1955, 1969, 1989 and 1991—and emerged victorious four times (including two wins by the lightweights, in 1951 and 1952).
 
The Grand Challenge Cup
1901 – SECOND, lost in final to Leander Club (England)
1955 – CHAMPION, defeated Vancouver (Canada) in final
1962 – Lost in semifinal to Moto Guzzi (Italy)
1969 – SECOND, lost in final to S.C. Einhert (East Germany)
1970 – Lost in first round to British National Team
1984 – Lost in first round to British National Team
1986 – SECOND, lost in final to Nautilus Boat Club (England)
 
The Temple Challenge Cup
1997 – Lost in semifinal to Cambridge's Goldie Boat Club (England)
 
The Ladies' Challenge Plate
1987 – Lost in first round to Vesta Rowing Club (England)
1989 – Lost in semifinal to Harvard
1991 – Lost in first round to University of London (England)
1998 – Lost in semifinal to Harvard
 
The Thames Challenge Cup
1955 – Lost in semifinal to Royal Air Force (England) in row-over after tie in first race
1969 – SECOND, lost in final to Leander Club (England)
1989 – Lost in semifinal to Ridley College (Canada)
1991 – CHAMPION, defeated the University of London (England) in the final
 
Lightweights in The Thames Challenge Cup
1951 – CHAMPION, defeated Florsheim-Russelsheim (Germany) in the final
1952 – CHAMPION, defeated Christ's College (England) in the final
1976 – Lost in semifinal to Henley Rowing Club (England)