awards

Most Charming Smile award 
from Witch Weekly Magazine

Medal for Magical Merit 
Given to Tom Riddle 50 yrs ago (CS13)

award for special services to the school
Gold shield awarded to Tom Riddle (CS13)
Harry and Ron received Special Awards for Service to the School (CS18)

Dangerous Dai Commemorative Medal
given each year to the Quidditch player who had been the most reckless, in honor of "Dangerous" Dai Llewelyn, a notably spectacular player for the Caerphilly Catapults (QA7).

trophies

House Cup
won each year by the House which earns the most House Points

Quidditch Cup
won each year by the top House Quidditch team

Triwizard Cup
Awarded to the winner of the Triwizard Tournament and held as an honor by the victorious school until the next tournament.

trophy for the winner of the annual broom race in Sweden
shaped like a Swedish Short Snout dragon (since the race runs through the Swedish Short Snout reservation, which thins the ranks of contestants somewhat)(QA)

Gryffindor Quidditch shield
In the film version of SS, a shield is shown with several names on it. At the top it says "Gryffindor" and prominently displayed in the center is a small shield with James Potter's name on it, listing him as playing Seeker in 1972. The other names are R. J. H. King (1969) and M. G. McGonagall (1971). Since Rowling has stated that James played Chaser, this plaque cannot be considered canon, although, as several fans have noted, there's no particular reason why James couldn't have played more than one position during his years on the team. Since we know that James was born c.1960, this would suggest that he won the award early in his years at Hogwarts.

honors
Order of Merlin - First Class (Dumbledore), Third Class (Lockhart), Peter Pettigrew (posthumous, supposedly)

contests
annual Daily Prophet Grand Prize Galleon Draw - 700 Galleons (PA1)

Quidditch titles
European Champion
Winner of the Britain-Ireland League
World Cup

Trophy Room
Hogwarts has a trophy room where all the old awards, trophies, statues, cups, plates, shields, and medals are kept in crystal display cases. There is also a list of all the head boys and girls. It's adjacent to a long gallery full of suits of armor. (SS9; CS7, 13). Peeves likes to bounce around the trophy room (PA10, GF25).