Smith played youth football for Brentford, Chelsea and Gillingham, before playing non-league football for Sevenoaks Town, Sittingbourne and Folkestone Invicta. While at Folkestone Invicta he had trials at Aberdeen, Gillingham, and Millwall, before signing a two-year professional contract with Millwall in August 2016.[5] He made his debut for Millwall on 8 November 2016, scoring twice in an EFL Trophy game against Luton Town.
On 12 July 2017, Smith joined League Two side Swindon Town on a season-long loan. On the opening day of the 2017–18 campaign, Smith made his Swindon debut in their 2–1 away victory against Carlisle United, replacing the injured Luke Norris in the 34th minute. On 30 September 2017, Smith scored his first goal for the club during their 2–0 home victory over Cambridge United, doubling Swindon's advantage in the 88th minute after ex-cobbler Keshi Anderson had given the Robins the lead. On 26 December 2017, Smith's loan spell at Swindon was terminated following a lack of game time.
He was released by Millwall at the end of the 2017–18 season.
On 4 July 2018, Smith opted to join newly-promoted League Two side, Macclesfield Town on a one-year deal.
Northampton Town have signed Macclesfield Town striker Harry Smith for an undisclosed fee.
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