At the age of 30 he gave up sales and marketing to pursue his calling as a coach and ended up in the MLS for two years. He's now moved to Seoul to start again...
There are key differences - largely off the pitch - but Liverpool fan Sam Drury has spotted five things that are similar five years on. A big sale, a big Italian arrival...
1. Which Matthew is the youngest ever player in Premier league history?
2. Which Matthew was signed by Ipswich from Sampdoria in 2001 for a club record fee?
3. Other than Arsenal, which other two clubs has Mathieu Flamini played for?
Marseille and AC Milan
4. Who was the only goalkeeper to save a Matt Le Tissier penalty in professional football?
5. Which Matthew was named Dutch Player Of The Year in 2003 before moving to London a year later?
6. Which Premier League Matthew is an England one-cap-wonder?
7. Which Matthew scored a brace in the Greek Cup final in 2009?
8. Which Matthew scored a brace to upset Liverpool in the 2013 FA Cup fourth round?
Matt Smith (Oldham)
9. Which Matthew scored Leicester City's fastest ever goal after 9 seconds of a match against Preston in 2006?
10. Which Matthew made 18 appearances for Scotland despite being born in Wandsworth, London?
11. And, similarly, which Matthew got 49 caps for Ireland despite being born in Bury?
12. Which French Matthew's career path read: Le Havre - Nottingham Forest - Norwich?
13. Which Matthew scored his first ever goal for Newcastle in the Tyne-Wear derby?
14. Which defender Matthew played the majority of his career in London and briefly had a column writing for the Daily Mirror?
15. I was signed from a Midlands club for £3.5million in 2002 as a highly-rated youngster, but injuries blighted my career and I made just 13 Premier League appearances for the club. Who am I?
16. Leeds - Sheffield United - Sunderland - Blackburn. Name me.
17. Which international Matthew has spent his entire top flight career at Marseille?
18. Matt Busby managed Manchester United to great effect, but do you know which two English teams he played for?
Liverpool and Manchester City
19. Which Matthew joined Everton on loan from Roma in 2005? He had a good engine.
20. Matthew Etherington joined Spurs from Peterborough in a deal with which other player?