Brightwell became known as a versatile player who played at every single outfield position during his career at the club; however, he was most commonly used either as a right-back or on the right side of midfield.
He did not score many goals but did memorably shoot into the top corner from 25 yards (23 m) on 3 February 1990 to earn City a draw with rivals Manchester United at Old Trafford.
New manager Brian Horton led the club to disappointing 16th and 17th-place finishes in 1993–94 and 1994–95; Brightwell did not feature in the first-team however, as he snapped his patella tendon, and was sidelined for more than a year.
He did eventually recover and returned to the City line-up for the 1995–96 campaign under Alan Ball, but could not prevent the "Sky Blues" from being relegated in 18th spot, finishing behind Southampton due to their inferior goal difference.
He was given a testimonial match and a free transfer, having made 382 league and cup appearances, scoring 19 goals, in an 18-year association with the Maine Road club.
He was loaned out to First Division side Walsall at the end of the 1999–2000 campaign, playing ten games, but could not prevent the "Saddlers" from suffering relegation.
Despite Walsall's relegation, Brightwell had impressed manager Ray Graydon during his time at the Bescot Stadium and joined the club permanently in the summer of 2000.
He played the full 120 minutes of the play-off final at the Millennium Stadium, as Walsall beat Reading 3–2 after extra time, having to come from behind twice in the game.
[5] In August 2002 Brightwell moved on to local rivals Port Vale, who were back in the Second Division under the management of his former boss at Manchester City, Brian Horton.
[13] He appeared in the Master's Tournament at the 2009 HKFC International Soccer Sevens, and began working at BBC Radio Manchester as a co-commentator.