Ainscough was promoted into Wigan Warriors first team on 22 January after receiving the number 28 shirt, which previously belonged to fellow academy product Sam Tomkins the season before. His first Super League game was in a 22–28 home defeat to Castleford Tigers, a match in which he scored his first Super League try which looked to have given Wigan a chance of winning the match until Castleford scored another try through Michael Shenton.
However, Ainscough made a lasting contribution in his next appearance against Harlequins RL at the Twickenham Stoop, in which he and Amos Roberts scored late in the match to give Wigan their first home win of the 2009 Super League season. Ainscough then featured in the Wigan team that defeated Bradford by 34 points at the JJB Stadium, before scoring a try on the way to a defeat at Leeds the week after.
An away win to Salford City Reds in which he personally contributed two tries was to be the last win in the Super League for some weeks for Ainscough. Although a home defeat against Huddersfield was followed by a hat-trick performance at Barrow in the 2009 Challenge Cup (a game in which the Warriors were pushed hard by Barrow), two further defeats at home to St Helens and away to the Catalans Dragons in Perpignan forced Wigan coach Brian Noble into changing the squad around, and even though Ainscough had contributed the only two tries of the night for Wigan against St Helens, he found himself out of the new squad, with Noble favouring Pat Richards and Amos Roberts on the wings with George Carmont and new Warrington-signing Martin Gleeson at centre, and Cameron Phelps at fullback for the Warriors' next game against Crusaders.
The brief hiatus broke the very next game, however, as Ainscough (who had been omitted from the initial nineteen-man teamsheet) was called up late to replace a tonsillitis-stricken George Carmont. He personally ran-in four tries to secure a 26–40 victory against Wakefield Trinity Wildcats at Belle Vue, to the praise of commentators in the British mainstream national newspapers, and drawing comparisons to the Wigan legend, Martin Offiah. The match brought his Super League tally of tries for the season to thirteen, the most of anyone in the league by that point. Despite this, Ainscough has only appeared in two more matches to date – an away defeat to Warrington, and another away defeat to Celtic Crusaders.
His capabilities in defence drew criticism from some coaches, not least his own coach at Wigan. Following the game at Wakefield, Noble stated that, "there are other parts of his game he needs to improve." In a pre-match interview before the Magic Weekend in Round 12, St Helens coach Mick Potter stated he was a target for high kicks, with the belief that Ainscough's opposite winger Ade Gardner, the leading try scorer in 2008's Super League XIII, would put him under pressure. It was a game Ainscough did not eventually play in.
After losing his place, Ainscough continued to play in the reserves, although in August it was confirmed he had suffered scaphoid wrist damage and as a result would possibly be out for the rest of the 2009 season.
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