The Manitoba Music Educators Association donated the Jacob (J.P.) Redekopp Memorial Trophy to the Winnipeg Music Festival in 1999. Mr. Redekopp served as the Association President, and is remembered for embracing music education in its' broadest sense. This trophy is awarded for the most outstanding performance by a School Boys Chorus, Kindergarten to Grade 6, during the Festival.
| Year |
Winner |
| 1999 |
Sansome School |
| 2000 |
Mennonite Brethren Collegiate
Institute |
| 2001 |
Glenelm School |
| 2002 |
Garden Grove School |
| 2003 |
Strathmillan School |
| 2004 |
Balmoral Hall School |
| 2005 |
Julie Riel Grade 7 Choir |
| 2006 | St.
John’s-Ravenscourt Ensemble |
| 2007 |
Henry G. Izatt Boys’ Choir |
| 2007 | Henry G. Izatt Boys’ Choir |