He helped himself to 14 goals and 11 assists in all competitions for Tampines in the 2016 S.League season, outshining the former Arsenal and Liverpool midfielder Jermaine Pennant, who was also playing for Tampines, in the process.[6]
Warriors FC
Webb joined Warriors for the 2017 season.[7] In March 2017, Webb claimed to be the victim of slanderous racial abuse in an S.League match, stating that Balestier Khalsa player Raihan Rahman had used a derogatory term against him.[8] Webb scored six goals in his first seven outings for the Warriors but did not net in the S.League again until October in a 3–2 away defeat to Brunei DPMM.[6]
Return to Tampines Rovers
Webb returned to former club Tampines Rovers after a season with Warriors FC for the 2018 Singapore Premier League season, with the Tampines Head Coach branding him as one of the best wingers in Singapore.[9] He rejected an offer from a Portuguese 2nd tier side to re-sign for Tampines Rovers.[6]
At the end of 2020, he left the club and Singapore and announced that he would be returning to Canada to continue his career.[11][12]
Return to Canada
On 13 April 2021, Atlético Ottawa confirmed the signing of Webb for the upcoming season.[13] On 27 July Ottawa announced that the club had terminated Webb's contract by mutual consent due to a "personal situation."[14]
On 28 August 2021, Webb returned to the Canadian Soccer League to play with Scarborough SC and recorded two goals in his debut match against Toronto Tigers.[15] He featured in the ProSound Cup final against FC Vorkuta but was defeated in a penalty shootout.[16] He returned for a match on 5 June 2022, against Toronto Falcons where he recorded a goal.[17]
In 2023, he joined ProStars FC.[20] At the same time, he also played with Scarborough SC in the 2023 season, contributing a goal against the Serbian White Eagles on 15 July 2023.[21] Throughout the 2023 campaign, he would help Scarborough secure the regular season title.[22]
International career
In November 2015, he announced his desire to represent Singapore at the international level, subject to receiving a Singaporean passport.[23] He received permanent residency status in June 2017.[24]