Stewart began playing rugby league at the senior level in 1921 for the Power Board team in Cambridge.
[2] Two weeks later Stewart played for the Cambridge sub union representative team against the touring Ponsonby United side which featured a young Frank Delgrosso.
[3] With rugby league in its infancy in the Cambridge area Stewart played for the Power Board side and representative teams interchangeably throughout the year.
The first match for South Auckland was against Hawke's Bay on August 10 and saw his side win easily by 35 points to 3 with Stewart scoring a try after some lead up play by Huatahi Paki.
His Cambridge team won 16-14 over a City side which featured George Paki, Maurice Wetherill, and Tim Peckham.
[7] In the August 31 edition of the Waikato Times it was said of Stewart that he “is a tricky player who will reach big football.
After voting had taken place Stewart was announced as the winner and was presented with a gold football badge which had been given to the union by Ernie Asher of the Auckland Rugby League who had recently visited with the City Rovers side.
Although there were many talented players in the Waikato competitions the Auckland Rugby League was reasonably well established by 1922 and the City side featured George Davidson, Ben Davidson (who would go on to play for Wigan), Bill Davidson, Maurice Wetherill, Alf Townsend, George Paki, and Bert Laing, while Stewart was playing alongside Clarrie Polson, Wally Somers, Bill Williams and Lou Brown (who would go on to play over 300 games professionally in England).
Although given fewer opportunities his play was ahead of Wilson Hall… apart from that it is distinctly disappointing to the Cambridge League and the selectors will find that it is a mistake”.
They won the match 23-13 though Stewart took a knock to the head which saw one observer state that “for a long period in the first session he was quite dazed”.
[24][25] The match with Taumarunui was a defence of the Endean Shield which Hamilton had won off Lower Waikato two weeks prior.
On August 18 South Auckland played Wellington with Stewart in the five eighth position alongside F. Jackson, with Tim Peckham at halfback.
[27][28] He then played for a combined Cambridge-Hamilton team against Lower Waikato and he scored twice in a 31-25 victory at Victoria Square in Cambridge.
After two matches for Hamilton Athletic against the Frankton Albions, and United teams, Stewart transferred to Marist Old Boys in the Auckland Rugby League competition.
[33] The matter was discussed at length at the South Auckland Rugby League monthly meeting and it was eventually decided to grant him a transfer.
[34] After the transfer was granted Stewart made his debut for Marist in a round 5 match against Richmond Rovers in the five eighth position.
Stewart was to partner Wilson Hall in the five eighths positions against Peebles and Hector Cole in the Possibles side.
[36] On July 28 Auckland played the English side and after the match the New Zealand squad was selected to go into training for the first test with England.
In addition to this halfback Thomas McClymont was injured in the first test and so Stewart was pulled into the side to travel south.
Despite the unavailability of at least 3 potential halves Clarrie Polson and Frank Delgrosso were selected ahead of Stewart for the second test which New Zealand won 13-11.
Stewart’s opportunity came in the 3rd test where he was selected in the second five eighth position with Frank Delgrosso on his inside and Hec Brisbane his outside.
In the Otago Daily Times of 25 February 1931 it was reported that at about midnight Stewart's one year old child was bitten by a rat with the bite going through the baby’s left hand and “caused considerable bleeding”.