Pickering 1-0 Windsor City in the Ontario League Cup, Qualification Round 1 at Pickering Soccer Centre, Pickering.

Pickering won 0, drew 5 and lost 0 of their previous 5 matches (D–D–D–D–D), scoring 7 and conceding 7.

Windsor City won 1, drew 2 and lost 2 of their previous 5 matches (D–L–D–W–L), scoring 7 and conceding 12.

The two sides have met 7 times: Pickering 2 wins, Windsor City 4, 1 draw.