Ryan started his footballing career at Blackburn Rovers in 1996 as a promising right and left winger. He went on to win the U17 Premier League and reach the FA youth cup final against Everton playing against a strong team in front of 25,000 that consisted of Leon Osman, Francis Jeffers, Richard Dunne and Michael Ball.
Ryan went on to become a reserve team regular in forthcoming seasons and was rewarded with a four year professional contract. He soon transferred to Premier League rival Bolton Wanderers.
Sam Allardyce made Ryan a late signing in March 2000 as comparisons to fellow ex teammates Damian Duff and David Dunn were made by his new boss and assistant Phil Brown. He was awarded squad number 33.
With pace to burn and accurate crossing ability Ryan soon showed his potential in Bolton's reserve side and pre season games for the first team. He left Bolton Wanderers after only 18 months however, the arrivals of Jay-Jay Okocha, Youri Djorkaeff and many more big signings that summer making it difficult to break through for the youngster.
In 2001 Carlisle signed Baldacchino on a three year deal. Ryan was an instant hit with the club with an outstanding display of pace and trickery to help defeat Southend United away. Ryan was a regular for Carlisle before being prized away by Brooks Mileson and the mega spending power of Scottish new boys Gretna.
Gretna won everything in sight and dominated wherever they played. Scottish Third, Second and First division titles were won by Baldacchino in consecutive seasons, with Ryan being one of the star players along with Kenny Deuchar, Gavin Skelton and Chris Innes. Those four players gained the prestigious accolade of being the only four players in 100 years of Scottish history to play in all Scottish divisions with the same team. Baldacchino won most Man of the Matches, Goal of the Season and had a UEFA Cup goal on his way up the divisions. An impressive display against Dunfermline in the Scottish Cup in front of Celtic manager Gordon Strachan earned Baldacchino rave reviews. Hibs, Motherwell and Celtic all had regular checks on Baldacchino. Brooks Mileson once again showed his spending power and ambition by keeping hold of Baldacchino and he signed a new improved four year deal in December 2005 making him one of the clubs top earners.
Gretna arrived in style to the SPL breaking all records on their way and many players staying loyal to Gretna turning away potential big money moves on the way.
The season 2007-2008 was to be Gretna's last year as a club as they bowed out at the top when owner Brooks Mileson took ill in late February. Ryan was given squad number 7 and played against Rangers and Celtic that season as Gretna struggled to cope with life in the top flight. They were relegated at the end of the season.
Baldacchino transferred to VPL club Altona Magic in May 2008 and one year later he signed for New South Wales Premier League outfit Bonnyrigg White Eagles. Currently he is free agent and wants to play in the Maltese Premier League and wants to represent Malta.