[3] Later that spring he reached the final of Sussex County Lawn Tennis Tournament at Brighton, but lost to Robert Braddell.

At Wimbledon 1883 Stewart beat Harry Grove, Claude Farrer, Herbert Wilberforce and William Taylor and then lost in the all comer's final to Ernest Renshaw (despite taking the first set 6–0).

[4] He won his first title at Cheltenham in June 1883,[3] the same year he reached the final of the Sussex County Lawn Tennis Tournament spring event for the second time losing to Charles Walder Grinstead.

In June 1884 he won titles at Cheltenham and Waterloo[3] in July at Wimbledon in 1884 he lost in the first round to Ernest Browne.

In August 1884 Stewart won the prestigious Northern Championships at Liverpool in 1884 (beating Richard Sears, James Dwight, Ernest Browne and Herbert Wilberforce).