Liverpool had previously tried to loan Michael from Hearts in the 1894/95 season when they were seriously depleted in an important Test match that would decide their fate in the First Division. Hearts didn't release him and the Reds were relegated. A scribe at the Athletic News had the following first impression of Michael shortly after his arrival at Liverpool: "He is a very nice player – one of the big ones in a small compass, and can play on the wings or centre." He was also described as having been "the battering ram" of Hearts the previous season and "could charge into a bull elephant and still come off best," so it's pretty evident he made his presence felt. Michael got his chance in the side at outside-left when Becton was suspended by the club for a couple of months after missing training. Michael regained a regular spot in the team in the last eight games of the campaign after Jimmy Ross had been sold to Burnley. The inside-forward scored five times as the club comfortably held on to their first division status at the second time of asking by finishing in a respectable fifth place. Liverpool wanted to keep Michael and offered him a "big sum down" and £4 per week for renewing his contract, but he wanted a return to Scotland and his old club, Hearts, re-signed him ahead of Hibernian, Celtic and Rangers.

Michael was the top scorer in the Scottish First Division in the 1899/1900 season, alongside the goal machine who was Rangers' Bobby Hamilton, scoring 15 goals.