During World War I, he enlisted on 23 October 1915[8] and served in the United Kingdom with the Manchester Regiment[9] in the Labour Corps, and was awarded the 1914-1915 Star[10] He then was assigned to the 29th Trench Mortar Battery with the Salonica Force fighting in Valletta, Malta.

The Great Depression, especially harsh in Australia,[17] resulted in there being few art lovers buying, or even showing interest in, sculpture with even the most professional failing to sell a single work.

In 1930–31, with the assistance of 17-year-old Stanley Hammond, he cast two identical groups of large figures of Faith, Hope and Charity, for placement six stories above the Collins and Swanston Streets entrances of the Art Deco Manchester Unity building.

The design is symbolic in character, and expresses civic pride by the seated central figure with the arts and culture on one side and the goldmining, which was responsible for the birth of Castlemaine, on the other.

In its next ten years until its demise because of the War, the Society promoted seven competitions for major public sculptures, of which Bowles won four, Hammond two and Anderson one; while none of the other members were successful.

In April 1933 the first group exhibition of sculpture to be held in Melbourne was organised by members Dutton, Bowles, Wallace Anderson, Ola Cohn, George Allen, and Charles Oliver.

[22] Arthur Streeton enthusiastically welcomed the exhibition and expressed surprise that Australia, which had a clear atmosphere and a suitable climate to show sculpture to its best advantage, did not make more of it.

In December 1935 Dutton submitted for the (Sir John) Monash Equestrian Memorial commission a finished maquette as one of the competitors, with Paul Montford, Lyndon Dadswell, Raynor Hoff, Wallace Anderson, Henry Harvey and A. de Bono, whose entries apart from that of winner, who again was Bowles, were exhibited in Melbourne at the new Arts and Crafts Society gallery.

[26] Dutton's architectural decoration continued in 1938 with his contribution of a symbolic bas-relief to the facade of Anzac House in Collins Street of a man holding high the Lamp of Honour while crushing the Serpent of Evil with his heel.

[30][31] During World War II Dutton again served, enlisting at Caulfield in the 2nd AIF with the service number VX22013,[32] and as an older recruit in his late forties his skills were employed in the Mapping Division making landscape models for training purposes.

Since the late 1970s a section showing eastern Australian states has been displayed in the School of Earth Sciences' Fritz Loewe Theatre, Melbourne University on the corner of Swanston and Elgin Streets, Carlton.

[44] Made its president in 1946–47,[45] he encouraged sculptors to join and founded a sculpture group,[46] inaugurating in 1947 an annual exhibition of the medium at the VAS in the first of which he included a life-sized Orpheus.

[53][54] Well versed in, and habitually applying, allegory in his art, at the August 1935 meeting of the Victorian Institute of Architects Students Society, Dutton described the preparation of scale models and sculpting techniques in the execution of large stone carvings with reference to his work on the spire of St. Paul's Cathedral.

[56] Asked in 1935 to comment by The Herald on Jacob Epstein's sculpture Behold the Man, Dutton, described as "noted ecclesiastical sculptor" gave a less reactionary, but still ambivalent, response than the others including Paul Montfort who called it "a bit of bunkum", saying; "There are two aspects in which to look at the work.

"[57] In 1936 his presentation on ABC radio station 3AR, was titled 'A Sculptor at Work' as part of a series 'An Australian Period' devised by R.H. Croll, whose portrait bust by Dutton was awarded the Melrose Prize in 1938.

[59] The article mentions Arthur Fleischmann and Lyndon Dadswell, but is illustrated only with Dutton's The Torch Bearer and Iris (purchased in 1954 by the NGV),[60] and quotes him as attributing the problem to "the Impact of Impressionism" as "detrimental to appreciation of sculptural form" and calling for a "return to formal relationships, composition and design," as seen in the then current painting, to "contribute to a readier understanding of these qualities in stone.

"[62] and of the 1940 spring show at the same venue remarks that in "a sculptured head of Harley Griffiths, the artist, Orlando Dutton, has been happy in catching the illusive [sic] smile of his sitter."

In the sculpture section of the fifth Australian Academy of Art exhibition held 20–31 July 1943, The Age, beside Bowles' work "of a more stylised type," rated Dutton's portrait of Dr. Austin Edwards as "probably the best.

[66][67] In 1962 he submitted a painting Friday Night to the Crouch Prize at the Ballarat Art Gallery which was noted by critic Arnold Shore as being of "special worth.

After a reported sighting of him in Chadstone,[72] police surmised he may have been suffering dementia,[73] though he had written in June a clearly argued letter to the editor of The Age,[74] and in August had joined with Alan Sumner, principal of the Prahran College, in a deputation to the State Government's Chief Secretary Arthur Rylah to advocate for appointment of Melbourne artists to the National Gallery of Victoria board of trustees.

[77] The Coroner conducting an inquest into his death in October found no evidence, or signs of violence, to show Dutton might have been pushed into the river, and could discover "no reason why he should have taken his own life," before returning an open finding.