Woodland was born in Abu Dhabi in the United Arab Emirates[2] to an English father and a Filipino mother.

[citation needed] Woodland was given a football scholarship aged 15 and a two-year professional contract at 17 years old in April 2013.

[8] His fourth appearance for Oldham, at home to Rochdale on 24 March 2015, saw him earn the man of the match award.

[12] After leaving Bolton, Woodland went on trial at Major League Soccer team New York Red Bulls.

[14] Woodland made his debut on 21 November 2015, coming on as a 75th-minute substitute for John Rooney in the 75th minute of a 2–1 home loss against Woking.

[5][32] While with Suphanburi, Woodland was involved in an altercation between himself and a Thai player while in a training session which caused him to loss favor with the club's non-English speaker coach.

Sustaining injuries after playing in the 2020 AFF Championship with the Philippine national team, Woodland returned to Buriram and took part in training to regain his form.

[citation needed] Two months later, he was named in the Philippines' 23-man squad for their 2018 FIFA World Cup qualifiers against Bahrain and Yemen on 11 and 16 June respectively.

[37] Woodland missed the match against Bahrain due to delays in gaining international clearance,[38] but made his debut against Yemen on 16 June 2015.