Sheffield United's decision to invest in Drummond in 1891 paid dividends when his goal in the test match at the end of the 1892/93 season against Accrington saw the Blades promoted to the First Division for the first time in their history. The pitch was in a terrible state and Drummond was practically the only player to be able to stay on his feet, which he attributed to painting the soles of his boots with black lead to prevent the mud from sticking. Drummond made 89 appearances for the club and scored 24 goals before joining Liverpool in the summer of 1884. Drummond played in 14 of 30 League matches in Liverpool's first-ever season in the First Division battling with fellow Scot Hugh McQueen for a place on the left-wing. The team struggled to come to terms with the top-flight and was immediately relegated. Drummond's only goal for the club came in the FA Cup, when he got the second goal in a 4-0 first round replay win over Barnsley St. Peter's. He joined Barnsley at the end of his career in the Midland league. Drummond had been an apprentice shipyard carpenter as a youth and returned to work in the Dumbarton shipyards after his retirement from football.