Football League career. A highlight of his season was the 5–2 defeat of Hartlepools United, in which he scored twice in the first 12 minutes, struck the crossbar, and left the field to a "storm of applause"; according to the Sheffield Daily Telegraph, the first goal "was a masterpiece. He beat three opponents by delightful footcraft, and hooked the ball into the net with such speed that Cowell scarcely saw it." When not scoring, he "contributed materially towards his team's success by his clever scheming and delightful passes" in support of the prolific Jimmy Cookson and others. Roseboom began the new season in fine form, scoring two "clever" goals, hitting the woodwork twice, and producing some "very pretty" scheming in a 5–1 win against Southport in mid-September, but the after-effects of an injury sustained two weeks later meant he was in and out of the team for some months, and not fully fit while in it. In December, he was dropped to the Midland Combination team for two matches, and submitted a transfer request. Having returned to the league side, he was omitted again, this time for a four-match spell, in March, but regained a place at inside left to accommodate Harold Roberts on the right and returned to form. He finished the season with 12 goals from 36 appearances in league and FA Cup. He appeared only intermittently at the start of the 1927–28 season, and when dropped early in December as one of seven changes made to the team, did not return until April. He made 18 appearances in league and FA Cup and scored four goals. In Ollie Thompson's benefit match, played against Northern Nomads, Roseboom converted a penalty in unusual style: he "gently kicked the ball, and it lightly sailed over and dropped into the back of the net, apparently much to the surprise of the goalkeeper"nearly 50 years before the original Panenka kick. Roseboom signed on for a fourth season with Chesterfield and resumed his status as a first-team regular. He scored in each of the first four matches, and took his total to eight from nine, including a last-minute winner away to his former club, Nelson. By Christmas, he had ten league goals and two in the FA Cup. While out injured, he was tasked with watching their third-round opponents, First Division team Huddersfield Town; Chesterfield lost the Cup tie 7–1. Once fit and