In the two seasons before the Football League was suspended for the duration of the First World War, he took his appearance total to 56 matches, and then returned to the north-east where he worked in shipbuilding before serving in the Royal Engineers.

He then spent one last season in the Football League with Third Division Crewe Alexandra before returning to his native north-east of England where he played at non-League level for a further three years.

[13][14] Arsenal lost 5–0, and the Daily News' reporter thought their forwards' shooting was the worst he had seen all season and "the only member of the line who was not greatly at fault was Winship, a small youth who was playing as outside left and delighted the crowd by sprightliness and accurate centring from all positions.

[16] He had a run of seven league matches, counting the visit of Aston Villa abandoned because of bad light, before Charles Lewis took over at outside left and David Greenaway returned to the side on the right wing.

[14][17] Winship came into the team for the visit to White Hart Lane, a heavy defeat, before returning to the Manor Ground to play a major role in the 3–1 win against their London rivals.

Described by the Daily Mirror as having the ideal build for work in the muddy conditions, Winship crossed the ball to set up Lewis's close-range opening goal.

[14] In mid-March, he was carried off the field with what the Daily Express called a nasty leg injury in a match against West Bromwich Albion and played no further part in the first team that season.

Questions were asked as to the probity of the transfer – Sir Henry Norris had been and remained a director of Fulham before becoming major shareholder in and chairman of Arsenal[24] – but the Football League's management committee ratified his return.

[27] The following year he guested for Ashington in Easter fixtures against Blyth Spartans,[28] and was expected to appear for Leeds City at Grimsby Town in the Midland Section of the wartime league competition, but did not.

[29][30] By November 1917, listed as Sapper Winship, he was guesting for Grimsby for their visit to Leicester Fosse,[31] and in September 1918, he was a member of the Royal Engineers Reserve Battalion team that won a five-a-side tournament in aid of the Football National War Fund.

[10] In December 1918, after the war ended but before his demobilisation, Lance-Corporal Winship played for the 1st Royal Engineers stationed at Newark, Nottinghamshire, against a Derby-based eleven featuring the former England international Steve Bloomer, who was making his first footballing appearance since his return from a German prisoner-of-war camp.

[40] Darlington faced Second Division Birmingham in the second round without centre forward Dick Healey, and according to the Yorkshire Post's reporter, in his absence "there were long spells in the game when Winship, who is very clever when he gets an opening, was left without the slightest chance of gaining distinction.

[37] Within the first minute of Darlington's first Football League match, at home to Halifax Town on 27 August 1921, Winship made a run down the left wing and crossed towards Bill Hooper, whose "driving shot"[46] was "in all probability" the first goal scored in the new division.

[53] In March 1923, after he scored twice against Bradford, the Derby Daily Telegraph described him as "quite the most consistent forward in Darlington's weak attack" whom "no inducement has yet proved sufficient" to persuade to leave.

In their first defeat of the season, away to Rochdale in mid-September, the Athletic News reported that "Winship was the pick of the Darlington forwards, and several of his early centres should have been turned to good account",[59] and two weeks later he produced a "swinging shot which curled into the net" to open the scoring at home to Bradford.

[70] The Derby Daily Telegraph wrote in December that he had been one of Crewe's most consistent players of the season thus far, that his experience counted for much, and despite his advancing years, he was still capable of being a "very powerful and dangerous raider".

[72][73] Appearances in the last three fixtures of the season took his total to 23 in senior competitions for Crewe, and put an end to a Football League career in which he scored 25 goals from 224 matches.