[10] During the 1995–96 season, Tyler failed to make an appearance for Peterborough,[11] spending time out on loan with Isthmian League First Division club Billericay Town.

[16][17] In the 1997–98 season, with Peterborough now in the Third Division, Tyler established himself as the club's first-choice goalkeeper at the age of 20, playing in every league game and making 57 appearances in all competitions.

[21] By now an ever-present in the Peterborough first-team, Tyler regularly played in over 40 games per season, and was named in the 2001–02 PFA Second Division Team of the Year.

[22] His career was not without injuries: a punctured lung sustained in 1999 kept him out of the team for a month, while a recurring wrist and hand fracture led to spells on the sidelines, particularly in early 2003.

[36] His loyal service to Peterborough resulted in a testimonial match organised by the club against Liverpool on 21 July 2007, in a game watched by a crowd of 9,339 fans.

[37] On 15 June 2009, with the realisation that the opportunity for first-team football at Peterborough was becoming increasingly rare, Tyler had his contract cancelled by mutual consent.

[40] Many players from his time at Peterborough were now in the Luton dressing room, including Shane Blackett, Claude Gnakpa, Liam Hatch, Adam Newton and Alan White, with Tyler admitting he would have no problems settling into his new club.

[52] The 2011–12 season saw him dropped at times for second-choice goalkeeper Kevin Pilkington though, in December 2011, Tyler signed a further contract extension to keep him at the club until the summer of 2013.

[53] Following Pilkington's decision to join Notts County as goalkeeping coach in February 2012,[54] Tyler played in all games, including the 2–1 defeat to York City in the 2012 Conference Premier play-off final.

[citation needed] Tyler continued as first-choice goalkeeper for the 2014–15 season, making 31 league appearances,[68] keeping 14 clean sheets and triggering a one-year contract extension in the process.

[71] In the 2015–16 season, Tyler sustained a back injury eight minutes into the first game under the tenure of new Luton manager Nathan Jones, a 0–0 draw with Cambridge United on 16 January 2016.

[74] However, Peterborough chairman Darragh MacAnthony later clarified the situation, claiming that Jones was "misinformed" and in fact an approach was made for Tyler's services, but was turned down by Luton.

[79] However, Tyler's situation changed once more when it was revealed a re-occurrence of his back injury would keep him out for the rest of the season, as talks with Peterborough resumed about a potential return.

[82] On 8 March 2016, Tyler's return to former club Peterborough United was confirmed as a player-coach on a three-month loan deal with a view to a permanent move.

[84] Tyler agreed a one-year permanent playing contract alongside his role as goalkeeping coach following the appointment of Grant McCann as Peterborough United manager on 16 May 2016.