Today, the pair will be reunited but in opposite technical areas as Plymouth Argyle take on Birmingham City at Home Park.
Argyle's director of football will take interim charge of the Pilgrims, along with long-serving coach Kevin Nancekivell, for the first time since Steven Schumacher quit to take over at Championship rivals Stoke City. There is a certain irony, therefore, that Dewsnip's debut in the Argyle technical area will come a few yards away from Rooney.
Dewsnip said: "I probably came across Wayne when he was nine, 10 years of age. I worked with not just Wayne but his two younger brothers (Graham and John) as well. I know the family extremely well. He will find it quite amusing that it's going to be me on the touchline I'm sure."
Rooney was appointed by Birmingham in October as the club's new American owners replaced John Eustace with him even though Blues were sixth in the table at the time.
Birmingham's good start to the Eustace had season under included a 2-1 win against Argyle at St Andrews in August, when Jay Stansfield scored in the fifth minute of added time to clinch the victory.
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