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Town edged out Middlewich 3-2 in the divisional cup at the CBS Stadium.
St Helens took the lead midway through the first half when Dek Hill slipped a through ball to Ben Noonan, who finished confidently.
Middlewich turned the game around early in the second half with two quick goals on the break from Taafe and Nash.
Town responded with a moment of quality when Noonan's cross was back-heeled into the net by Hill to level the score.
Hill struck again minutes later, firing home a half-volley after the ball bounced around the penalty area.
Supporters were full of praise for debutant Adam Palfrey. He created a couple of opportunities for teammates and nearly scored himself with a late effort.
Noonan was named St Helens Borough Food Pantry player of the match.
Town return to league action this Saturday with a home fixture against Bollington, kick off at 3pm.