Overview
The first ever player signed by the team was Canadian defender Zachary Sukunda on 29 November 2018, followed by a quartet of Trinidad & Tobago players in the new year. A contingent of Canadians followed before Hart turned his attention to signing three players from the CPL Open Trials: [1] Kouamé Ouattara, Kodai Iida, and Mohamed Kourouma. Hart also signed all three U-Sports draft picks, and added some veteran attacking options in Luis Alberto Perea and Juan Diego Gutierrez. As the season approached and during the season, Hart raided League 1 Ontario club Vaughan Azzurri three times to round out his squad, signing Tomasz Skublak, Matthew Arnone and eventually, Duran Lee.
A short pre-season in April in the Dominican Republic saw HFX play only two matches, before playing its first ever competitive fixture on 28 April 2019, away at Pacific FC and losing 1–0. Following the defeat, HFX returned home to a raucous Wanderers Grounds on 4 May 2019, picking up its first win in history, defeating eventual champions Forge FC 2–1 with forward Akeem Garcia, scoring the team's first ever goal in the 30th minute. HFX would finish the Spring Season a respectable fourth place. In the Canadian Championship, HFX dispatched Vaughan Azzurri and Valour FC.
The Fall Season began optimistically on 6 July 2019 with the team recording a 1–0 win over York 9 FC and preparing to face Ottawa Fury FC of the United Soccer League Championship in the third preliminary round of the Canadian Championship. However, a congested fixture schedule would take its toll on the team, playing seven matches in eighteen days in July. HFX would lose all of them, bar one draw away to the afore-mentioned Ottawa Fury FC, which was insufficient to progress in the Canadian Championship. Throughout the year, HFX had had difficulty mustering much offense, which contributed to the slump. Improved defensive performances in September resulted in an uptick of form, but without much goalscoring, HFX could only muster six consecutive draws (a league record), surrendering the lead late on a number of occasions along the way. Combined with suggestions of locker room discord [2] and Hart commenting on his players learning what it meant to be a professional, [3] the Fall Season was difficult for HFX, finishing last which also “earned” the team the proverbial wooden spoon for 2019 as a whole. However, the year would end on a positive note, with Hart and company earning their first and only away win, 2–0 against York 9 FC. The Privateers 1882's supporter's group player of the year award went to centre-back, Matthew Arnone.
Off the pitch, the club was a tremendous success, the supporters regularly packing Wanderers Grounds to its limits and making it a difficult place to play for visiting teams. Indeed, in league play Cavalry FC was the only team to ever win at Wanderers Grounds all year. The boisterous atmosphere was the envy of the league and even attracted the notice of Toronto FC captain Michael Bradley who hoped his team would play there in the Canadian Championship. [4]
A last place finish, however, was always going to mean high player turnover. Instead of announcing a list of players released at the end of the season, the club instead would announce returning players only over the course of the off-season. [5]
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