[2] Alessi joined the Western Sydney Wanderers on 13 October 2013 on a Youth League contract for the 2013–14 season.
[3] Alessi played his debut game in the senior team in the second Sydney derby of the season on 11 January 2014.
[7][8] On 19 February 2018, after not playing for the club, Alessi was released by Newcastle Jets to allow him to take up an opportunity at Manly United.
[9] On 11 January 2020, Alessi joined Southern League Premier Division Central side Stratford Town, on dual registration from Hereford.
[11] Alessi returned to Australia, signing with National Premier Leagues club Blacktown City in July 2020.