Most unexpected team qualifier: men’s field hockey
Most unexpected individual qualifier: probably Daniel Gaysinsky in karate.
Team that failed to qualify that hurts the most: men’s baseball from a medal perspective, men’s basketball from an importance perspective. The women’s 3x3 team not even having a chance to qualify was a bitter pill, too.
Athlete that failed to qualify that hurts the most: Haya Jumaa in karate since she is probably the highest ranked Canadian athlete in any sport to fail to qualify (not counting internal selection), and she will likely never get another chance. The Christa Deguchi / Jessica Klimkait internal selection battle in judo was also really painful.