After playing his way through the Spurs youth set-up and being part of the Lilleshall FA Academy, Chris Day moved on to play for a number of clubs in the lower divisions and non-league, before returning to the Football League with Stevenage.

Day started off as a striker in the same boys team in Chingford as David Beckham (Ridgeway Rovers), but despite being taller than anyone else at the age of 10 and scoring 63 goals in one season, Day found himself donning the gloves.

When released by Spurs just before he was 21, he moved to Crystal Palace, where he played over 20 games in the season, but was dropped in favour of Carlo Nash, who went all the way to Wembley with the club in the play-offs.  At the end of the season, Palace wanted a more experienced keeper and signed Kevin Miller from Watford and Day moved to play under Graham Taylor at Vicarage Road as part of the deal.  Ironically, he didn't play much under Taylor, as Alex Chamberlain was always his number one keeper as they won the Division Two title and won the 1999 play-off to reach the Premier League.  Chris did get his chance at the start of the 1999-2000 season, when Chamberlain was injured and he played 11 Premier League games, including keeping a clean sheet at Anfield in a 1-0 win over Liverpool.

It was another Spurs keeper, in the shape of Espen Baardsen, who was signed in the summer of 2000, who once more ousted Day from the Watford side.  To get some playing time, he moved to Lincoln City on a three month loan spell and at the end of the season, left Watford on a free transfer to join Queens Park Rangers, who had just been relegated to Division Two.

At Loftus Road, he kept the gloves until October 2001, when he was dropped and then when he did return, he sustained a broken leg in a game with Oldham Athletic, which kept him out for almost a year.  Part of his rebuilding process was to go on loan at Aylesbury United, but he suffered another injury when he got back into the first team.

Rangers got back into the Championship by earning promotion in 2004, with Day taking his place between the posts for the start of the campaign, but when he fell out of favour once more, in January 2005, he was allowed to go out on loan to Preston North End to gain some confidence.  It wasn't helped when he returned to QPR to find Simon Royce had been signed as a permanent keeper and with no prospect of regular football, Day left in the summer to join Oldham Athletic.  A season there saw him replaced firstly by Derby County keeper Lee Grant, who was on loan and then Les Pogliacomi, resulting in Chris returning to London to sign for Millwall. 

After a couple of seasons with the Lions, he was released and had a trial with Watford, but was only signed on as cover for first choice keeper Scott Loach, so didn't actually get to play.

Chris moved to the Broadhall Way stadium in the early part of 2008-09, taking over as the first choice goalkeeper and was part of the Stevenage team who got to the play-offs, but lost in the semi-finals, although at the end of that week, the team went to Wembley to beat York City 2-0 in the final of the FA Trophy.  Played a significant par tin Stevenage gaining promotion from the Conference to the Football League and played in the club's first match in League Two at home to Macclesfield Town - a proud moment for the keeper, who is now resident in the town and owns the Crooked Billet pub, about a mile from the Broadhall Way ground.

Chris had an even better day at Old Trafford in 2011, when Stevenage gained promotion to League One via the play-offs, beating Torquay United.