He has played under three different managers at Oriel Park, Trevor Anderson, Jim Gannon and John Gill.
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Sean Connor, the new Dundalk manager, stated that Bennion will remain Dundalk's number one choice in goal despite the fact that the majority of the 2008 First Division winning squad were released.
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Just one month later in April 2002, he left Glanford Park for League of Ireland side Shelbourne on a free transfer.
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Middlesbrough won the game 2–1 thanks to two late goals from Noel Whelan and Mark Summerbell at the Riverside Stadium.
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