Mike Dean’s red card shown to Manchester United’s Ashley Young at Wolves was his 100th in the Premier League.

It all began in April 2001, when budding young(ish) referee Mike Dean administered a red card to Nolberto Solano of Newcastle United for deliberate handball in a 1-0 defeat at Ipswich Town.

A mere 18 years later, Dean brought up his century during Wolves’ 2-1 win over Manchester United on Tuesday night when he had the distinct pleasure of flashing a second yellow card in Ashley Young’s direction.

It was a truly momentous moment in Young’s career as he joined an elite band of players to have been sent off twice by Dean: Andy Cole, Fernando Torres, Laurent Koscielny, Mike Williamson and Richard Dunne.

Overall, 94 players from 33 different teams have had their afternoons ended early by the Grand Duke of Dismissals. Here’s our pick of the very best of them.

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