His stay was short and was soon back in professional football, signing a two-year scholarship with Southend United on 16 December 2002[2] following a five-game trial period.

On 22 October 2004, he joined Farnborough Town on loan,[6] spending three months with the club before returning to Southend United on 20 January 2005.

[8] Conference side Grays Athletic signed Kightly, where he scored 15 league goals in his first season, and won the FA Trophy.

Such form caught the eye of scouts at Championship side Wolverhampton Wanderers, to whom he completed a two-month emergency loan move on 17 November 2006.

His form at Grays Athletic led him to be dubbed "The Ryan Giggs of non-league football", and it was reported that Sir Alex Ferguson was interested in signing Kightly for Manchester United.

[11] After scoring two goals in five games, his loan move was made permanent when he signed a two-and-a-half-year contract for a nominal fee on New Year's Day 2007.

Kightly signed a new four-year deal with Wolves in June 2007,[13] after reported interest from Manchester United, Aston Villa, and Everton.

[14] His first full season with the club was severely hampered by a persistent ankle injury suffered in November 2007, from which he twice tried to return to first team football, eventually undergoing surgery in February 2008.

Despite Wolves struggling Kightly hit a rich vein of form towards the end of the season scoring three goals against Aston Villa, Bolton Wanderers and Stoke City.

[22] In August 2012 it was revealed by Wolves that Kightly was in talks with Stoke City, having rejected a contract extension to instead remain in the top flight.

[25][26] He made an instant impact with Stoke scoring with his first touch in a 1–1 draw with German side SpVgg Greuther Fürth in a pre-season friendly.

[32] In May 2013 Pulis was replaced by Mark Hughes and Kightly expressed his desire to become a first team regular under the new manager and also admitted he struggled with confidence in the 2012–13 season.