Heats and a final were again utilised for the fourteenth Head of the River on the Upper Yarra one mile course on 13th and 14th May 1881. Geelong Grammar again requested that the race be held on the Barwon but Scotch and Wesley did not agree. It was not until 1886 that it was agreed that the race should be conducted on the Barwon every four years.
Geelong Grammar finished second behind Wesley College in the heat by a length in a boil over - everyone expected a Geelong victory. Melbourne Grammar finished three lengths behind Scotch in their heat.
The final was close until Swan Street when Scotch drew away to win comfortably.
Starter: Mr Edward Carlile
Umpire: Mr A Nicolls
Judge: Mr J W Colville
Margin: 3 lengths
1st Scotch College - Bow: Gideon U Rutherford, 2: Samuel J McCulloch, 3: Charles A Finlay, Str: Herman F Lawrence, Cox: George E Lorimer, Cch: John Wallace
2nd Wesley College - Bow: S L Angwin, 2: J H Trahair, 3: J H Permewan, Str: E A Heath, Cox: J F Hester, Cch: G H Brown
Other crews competing:
Geelong Grammar - Bow: W L Robertson, 2: I P Manifold, 3: W Moffat, Str: R J M Broughton, Cox: J Bailey, Cch: J L Cuthbertson
Melbourne Grammar School - Bow: C R Matthews, 2: G F B Smith, 3: F W Osborne, Str: S A Bucknall, Cox: H G Wragge, Cch: Mr Miller
E1: 1st WC, 2nd GGS, Margin 1 length
E2: 1st SC, 2nd MGS, Margin 3 lengths
Margin: 5 lengths
1st Geelong Grammar
2nd Melbourne Grammar
Other crew competing:
1st GGS, 2nd WC. Margin 6 feet. MGS secured a bye.