The Challenge Trophy is played for every time the holder plays a scheduled 11-a-side competition game. The challenger must win, a draw retains the trophy.
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The holder at the end of the 2008 season is Waipukurau.
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           2008
Waipukurau (1)
Southern (1)
Elsthorpe (9)
           2007
Southern (?)
           2006
Southern (2)
St Josephs (1)
Western (6)
           2005
Western (11)
Terrace (1)
           2004
Terrace (3)
Sherwood (9)
Terrace (2)
           2003
Waipukurau (1)
Sherwood (7)
Flemington (4)
           2002
Flemington (3)
Takapau (1)
Waipukurau (2)
Flemington (2)
Sherwood (6)
           2001
Sherwood (2)
Waipukurau (1)
Sherwood (1)
Terrace (1)
Waipukurau (3)