Further signings from Wrexham took place when striker Simon Brown and midfielder Christian Smith signed on loan and permanently respectively. Hirst was released having failed to break into the first team. Lewes were beaten 3–0 at home; Brodie opened the scoring with a volley into the top corner from outside the penalty area, and Christian Smith scored from 30 yards before Brodie finished the scoring with a low shot into the bottom corner. Henderson was released having fallen out of the reckoning for a first-team place. York were knocked out of the Conference League Cup following a 3–1 away defeat by Barrow in the Northern section fourth round. Midfielder Levi Mackin was signed on loan from Wrexham until the end of the season. He debuted in York's 2–1 away defeat to Eastbourne Borough, in which Christian Smith scored a header from Brown's cross. Adam Smith rejoined York from Gainsborough on a permanent contract for an undisclosed fee. His return came as a substitute in York's 1–1 draw away to Altrincham, in which Brodie scored the equalising goal after Shaun Densmore put the home team in the lead. Farrell was loaned out to Oxford for the remainder of the season, as he sought more game time. York drew 1–1 away with Kidderminster in the FA Trophy third round, in which Boyes scored his first goal for York, meaning a replay was to be played. Critchell's loan at York was extended for a second month, with the fitness of several York defenders in doubt. York were beaten 1–0 away by Mansfield, courtesy of a Robert Duffy penalty, in the teams' fourth encounter of the season. A 13–12 penalty shoot-out victory over Kidderminster followed a 1–1 extra time draw in an FA Trophy replay; in normal time, McBreen scored a header from a corner delivered by Simon Rusk before the away team equalised shortly after through Justin Richards. A new record for the most consecutive penalties scored in a shoot-out was set, at 25. McBreen was reported to have signed for North Queensland Fury of the A-League, although the transfer had yet to be confirmed by York. It was confirmed that he would join the Fury for the start of 2009–10 in August 2009. Former Wrexham defender Shaun Pejic signed after a successful trial at the club. York beat Conference South team Havant & Waterlooville 2–0 at home in the fourth round of the FA Trophy to secure a place in the semi-final, with both goals scored by McBreen.