The defender is playing a full part in preparations for the Worthington Cup Final knowing he has to sit out the big one at Cardiff's Millennium Stadium on Sunday.
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'Deano' has been cup-tied throughout the run to the final after playing for Southampton against Brighton in the second round just before joining us in September.
He has admitted how difficult it has been watching from the stands and it's an experience Tim had to endure back in 1999.
The midfielder joined us from Blackburn in Febuary 1999 and six weeks later had to watch as we beat Leicester City in the Worthington Cup Final at Wembley.
Tim said: "It's obviously disappointing but there is nothing you can do.
"Dean played for Southampton just like I played for Blackburn before I came here in 1999. All you can do is wish the lads all the best and hope they win.
"To be fair, when we won it when I first arrived, it was a boost and set a nice platform for the rest of the season. It puts you in a bit more of a comfort zone."
Meanwhile, Tim's feelings have gone full circle since missing out three years ago.
Victory over Chelsea represented the first semi-final success of his long career and he's now preparing for his first final almost 15 years after his professional debut
"I've had seven semi-finals and that was the first one I've won," he revealed. "It's my first final so hopefully I can set a trend there. Hopefully I'll get my chance on Sunday and I'll take it with both hands."
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Tim Sherwood knows exactly what unlucky Dean Richards is going through this week.