[4][5] His only senior appearance was in a 2–1 defeat at Portsmouth in the 1901–02 FA Cup, playing at inside forward in a team weakened by injuries,[4][6] and in 1903 he signed for Blackpool.

[12] He had been so popular at Blackburn that a "crowd of players and friends", accompanied by the Palace Theatre band, saw him off at the station with renditions of "For He's a Jolly Good Fellow" and "Auld Lang Syne".

He remained in west London with another Southern League club, Queens Park Rangers, who had ended the previous season eight places below Brentford.

Playing at outside right, Pentland scored 14 goals from 37 Southern League matches,[15] and was selected for The South to face The North in an international trial.

[20] In June 1908, Pentland returned to the First Division with Middlesbrough,[17] who had to pay fees to both clubs with an interest in the player: £350 to Queens Park Rangers and £150 to Blackburn Rovers.

[12] Playing with such teammates as Alf Common and Steve Bloomer,[21] he helped Middlesbrough finish ninth in his first season,[22] and in 1909, was rewarded with his first cap for England.

He played at outside right, alongside captain Vivian Woodward, as England beat Wales and Scotland to complete victory in the 1908–09 British Home Championship.

[1] In the next two seasons, Pentland continued to play regularly, although Middlesbrough were less successful,[22][23] and in 1911 he spent some time suspended by the club for "neglecting his training".

[25] He scored freely, finishing the season as the club's top scorer,[26] as well as acting as player-manager,[27] and helped Halifax reach the first round proper of the 1912–13 FA Cup.

[27] He remained with Stoke until December of that year, contributing six league goals in twelve appearances, before returning to Halifax[26] where his career ended a few months later through injury.

During his recuperation, he met Nahneen Hayes, a war widow working as a nurse with a Voluntary Aid Detachment (VAD); the couple married in 1923.

The host nation, Belgium won the gold medal by default after Czechoslovakia walked off in protest during the final, unhappy with the performance of the referee and the conditions surrounding the match.

[36][40] In May 1929 he helped coach the Spain national team, under manager José María Mateos, when they beat England 4–3 at Athletic Madrid's Metropolitano Stadium.