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Scott Jones came off the bench to grab a late winner in this five-goal thriller.
Second half goals from Kenny Pogue and Tom Chalmers earned Hastings all three points as Chichester suffered a first loss in nine games in all competitions.
A stunning 25-yarder from midfielder Lloyd Rowlatt and another goal by right back Ryan Davidson with 10 minutes to go earned Chichester a first league win on the road this season.
Two outstanding saves from penalty shoot-out hero Kieran Magee after this Velocity Trophy tie finished goalless helped Chichester advance to the next round of the competition.
An early goal from top scorer Callum Overton and another after the break by Emmett Dunn, who grabbed the extra time Sussex County Cup winner against Whitehawk midweek, extended Chichester’s unbeaten run in the league to four games.
Chichester City FC is lending its full support to Play Safe – a national FA-led campaign to raise awareness of the importance of safeguarding in football.
An Emmett Dunn goal deep into extra time sent Chichester through to the next round of the Sussex Senior Challenge Cup.