His opportunity arose from a suspension crisis, the Maroons having no fewer than four defenders (Bruno, Weir, Ritchie and Pointon) sent off in their previous match at Rangers.
Within a year he had established himself as the side's first-choice left back, displacing Neil Pointon, and in 1998 helped the Tynecastle club end their 36-year trophy drought by lifting the Scottish Cup.
Financial concerns at the club heightened these and in October 2000 it appeared that Naysmith was bound for the West Midlands when Coventry City bid for him.
He kept his place after Valente returned to fitness, however it was not long before injury befell him again, a medial ligament strain in the game against Newcastle United on 24 September 2006 keeping him out for two months.
[9] On 5 May 2007, Naysmith scored the third goal in a 3–0 victory over Portsmouth The win practically guaranteed that Everton would be playing in Europe during the 2007–08 season.
Naysmith made over 130 Premier League appearances for the Toffees before leaving the club to join Championship side Sheffield United for £1 million in July 2007 as part of an exchange deal with Phil Jagielka.
As part of the deal that took Phil Jagielka to Goodison Park, Naysmith was given permission to speak to Sheffield United to discuss a possible move.
He was signed by The Blades and agreed a three-year deal at Bramall Lane, thus ending a six-and-half-year stay with Everton.
[12] Naysmith revealed that he turned down offers from Premier League clubs where he would have had the chance to be a squad player to move to the Galpharm Stadium.
On 14 August 2010, Naysmith was then sent-off in his home debut for the Terriers versus Tranmere Rovers, as the match ended in a 0–0 draw.
[14] After a successful trial and impressing in games against Werder Bremen and FC St. Pauli, Naysmith signed a one-year deal on 1 August,[15] but expressed a desire to earn an extension beyond the summer.
[22][23] On 31 October 2013 Naysmith agreed to stay with League One East Fife until the end of the season in a player-assistant manager role.
[31] On 4 May 2019, after the Doonhamers were defeated 3–0 at home versus Partick Thistle and finished in the relegation play-off place in the Scottish Championship, Naysmith parted company with the Dumfries club.
[32][33] In August 2019, Naysmith returned to Hearts in a newly created role of managing players loaned out to other clubs.