City lost the Championship play-off final in the cruellest way possible, losing 6-5 in a dramatic penalty shootout to Luton Town at Wembley Stadium.

Source: https://www.coventrytelegraph.net/sport/football/football-news/coventry-city-doug-king-cbsarena-28118706

The Dark Blues snatched all three points in the seventh minute of injury time through Joe Shaughnessy, inflicting the cruellest of defeats on the Staggies.

Source: https://www.pressandjournal.co.uk/fp/sport/football/ross-county/6295311/derek-adams-offers-brutal-assessment-of-scottish-football-standard/

We love football, but it can be the cruellest sport in the world.

Source: https://www.peterboroughtoday.co.uk/sport/football/peterborough-united/peterborough-united-chairman-positive-message-for-the-clubs-manager-and-fans-after-admitting-a-little-piece-of-him-died-after-the-play-off-disappointment-4151137