Complex sentence: Whilst on loan at Northwich Victoria, Bailey trained with Championship outfit Crewe Alexandra and scored twice in an under-18 game for "The Railway Men" and this performance impressed manager Dario Gradi enough to earn a one-year contract in May 2005.
Split into simpler sentences: Whilst on loan at Northwich Victoria, Bailey trained with Championship club Crewe Alexandra and scored twice in an under-18 game for "The Railwaymen". This performance impressed manager Dario Gradi enough to earn him a one-year contract in May 2005.