Since 2010-11, the Kestrel Cup and Peregrine Cup have been awarded to the female skater and male skater, respectively, who best displays adherence to the principles of True Sport, namely:
The names of the awards are in homage of wildlife in the Milton area that exhibit strategies and traits of a speed skater. The Kestrel is known for its unique hunting style in which it is known to hover above the ground before dropping on its prey. The Peregrine Falcon is known as the fastest bird on the planet with dive speeds in excess of 320 km/h while hunting. Like the Kestrel a speed skater hovers in the pack of a race before striking for the win, and like the Peregrine a speed skater’s goal is to be the fastest.
The Kestrel Cup and Peregrine Cup was first awarded in 2007, the third season of the Milton Speed Skating.
Todd Landon who started Milton Speed Skating in 2004 donated the awards in 2007.