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Dennis Bailey is one of the richest Association Football Player from United Kingdom. According to our analysis, Wikipedia, Forbes & Business Insider, Dennis Bailey's net worth $5 Million. (Last Update: December 11, 2023)

Bailey started his career at Watford playing in their youth and reserve sides between 1982 and 1984. He subsequently joined Barking, before joining Fulham on non-contract terms in November 1986. He signed for Farnborough Town in February 1987, before returning to league football in December 1987 with Crystal Palace, joining for a fee of £10,000. He was loaned to Bristol Rovers in February 1989, before joining Birmingham City in August of the same year. He was loaned to Bristol Rovers again in March 1991, but returned from his loan to feature as a substitute when Birmingham beat Tranmere Rovers to win the 1991 Associate Members’ Cup Final.

Bailey signed for Queens Park Rangers for £175,000 in July 1991. He made his debut on the opening day of the 1991–92 season against Arsenal, scoring in a 1–1 draw.

Bailey was loaned to Brentford in January 1995, before signing for Gillingham in August of the same year, helping them win promotion from Division Three that season. He subsequently played for Lincoln City, before moving into non-league football for a second spell with Farnborough Town. He then moved on to play for Cheltenham Town, Forest Green Rovers, League of Wales side Aberystwyth Town, Tamworth, Stafford Rangers, Moor Green and Stratford Town. He retired as a player in November 2006.