Chesterfield
In September 2008, Lee was attacked during a night out in Sheffield and required surgery after his jaw was broken. After returning to action, Lee became a fan favourite at Saltergate.
At the end of the season, Lee won the club's Young Spireites Player of the Season award, before signing a two-year deal to keep him at Chesterfield until June 2011. In May 2011, Lee was offered and signed a two-year extension, keeping him at the club until June 2013. Lee has been a firm favourite with the Chesterfield fans, his popularity easily notable as the goalkeeper picked up the fan-voted Player of the Year Award two years running.
Lee played every minute of the Spireites' championship-winning 2010–11 season. His fine form was rewarded as he was placed in the PFA Team of the Year for that season. In September 2011, Lee was injured in a game against Bury. The side missed him to the extent that without him they began a long series of matches without winning and slumped to the bottom of the League One table.
In January 2012, Lee was named man of the match in both legs of the Football League Trophy Northern Final, helping Chesterfield to a 3–1 win and their first trip to the new Wembley Stadium. In the final on 25 March 2012, Lee helped his team keep a clean sheet in a 2–0 win over the much fancied Swindon Town, making a crucial flying save to tip a header over the bar in the final minutes of the game.
In January 2013 Lee signed a three-year contract keeping him at Chesterfield until 2016.
Tommy Lee again found himself in the League 2 PFA Team of the Year, on the same day he kept a clean sheet against Burton Albion to take the Spireites back to League 1 on 27 April 2014.
On 22 July 2015, Lee signed a two-year contract extension, keeping him at the club until 2018. On 2 January 2016, Lee made his 300th league appearance for the Spireites in a 7–1 victory at home against Shrewsbury Town.
On 6 November 2017, Lee announced his retirement from football with immediate effect, aged 31, due to a recurring shoulder injury.
On 25 July 2018, Lee was honoured with a testimonial match against Wigan Athletic, managed by former Chesterfield manager Paul Cook. Lee started the match and played the opening six minutes before being substituted to a standing ovation. The match finished 1–1.
