Jason Montgomery (Victoria, BC) run at the 2020 Raymond James Kelowna Double Cash came to an end in the semifinals with a 4-2 loss to Tyler Tardi (Langley, BC). of the 2020 Raymond James Kelowna Double Cash in Kelowna, British Columbia, Canada; Montgomery advanced through the quarterfinals with a 9-8 win over Sebastien Robillard (Maple Ridge, BC). of the 2020 Raymond James Kelowna Double Cash in Kelowna, British Columbia, Canada;
 
Montgomery finished 2-2 in the 12 team Raymond James Kelowna Double Cash qualifying round, held November 6 - 8, 2020 at the Kelowna Curling Club in Kelowna, Canada. In their opening game, Montgomery defeated Erik Colwell (Kelowna, BC) 7-2, then went on to lose 8-7 against Steve Laycock (Vernon, BC). Montgomery lost 8-3 to Robillard where Montgomery responded with a 8-6 win over Neil Dangerfield (Victoria, BC) in their final qualifying round match.
 
Montgomery ranks 313th overall on the Year-to-Date rankings with 0.000 points earned so far this season.