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Armstrong was born in [[Newcastle upon Tyne]] to an Irish father and Nigerian mother, and moved to [[London]] at age three. He was raised by foster parents in Wales, where he began playing as an amateur [[Goalkeeper (association football)|goalkeeper]] in local leagues, before leaving school and giving up on football aged 16. A friend reintroduced him to the game by bringing him to [[Llay Welfare F.C.|Llay Welfare]] in the [[Welsh National League (Wrexham Area)|Welsh National League]], while he packed burgers during the day for £30 a week. He gained the attention of local professional club [[Wrexham A.F.C.|Wrexham]].<ref name=ten>{{cite news |title=Ten things you didn't know about Chris Armstrong |url=https://www.theguardian.com/football/1999/mar/25/newsstory.sport7 |accessdate=15 August 2018 |work=The Guardian |date=25 March 1999}}</ref><ref name=moore/>
At Wrexham, Armstrong made his professional debut as a teenager during the [[1989–90 Football League]] season in the old [[Football League Fourth Division|Fourth Division]], and managed to score three times through the course of the season. In his two-year spell at the club, he went on to play 60 games, scoring 13 times.<ref>[http://www.sporting-heroes.net/football/tottenham-hotspur-fc/chris-armstrong-5504/1995-96-2001-02_a12651/] Sporting Heroes - Extracted 24 January 2012</ref> He took part in the [[1990–91 European Cup Winners' Cup]], where he scored the only goal of the first round tie against Denmark's [[Lyngby Boldklub|Lyngby]] before elimination by eventual champions [[Manchester United]] in the second round.<ref name=moore/>
He moved to [[Bruce Rioch]]'s [[Millwall F.C.|Millwall]] for £50,000 in August 1991.<ref name=afp/>
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