New manager John Askey confirmed that Pope would continue in his role as club captain in July 2019. He was mainly used as a substitute at the start of the 2019–20 season, but started in his 500th game as a professional footballer in a 2–2 home draw with Mansfield Town on 21 September. On having to regularly sit on the bench, he went on to say "it has been the lowest point of my career really". He scored a brace in a 3–1 home win over Morecambe on 5 October to earn himself a place on the EFL team of the week. However, later that month he lost the club captaincy to Leon Legge after being increasingly started from the substitute's bench. On 30 November, Pope scored an eight-minute hat-trick to secure a 3–1 victory over Cheltenham Town in the FA Cup second round. In the following round he scored his 109th Port Vale goal, making him the outright second-highest goalscorer in the club's history (behind Wilf Kirkham), in a 4–1 defeat to Premier League champions Manchester City on 4 January. This was later named as Port Vale's goal of the season. He had previously criticised Manchester City and England centre-back John Stones on Twitter, saying he'd "get 40 a season" playing against Stones every week, and after the game tweeted that "I was completely wrong and bang out of order to say I'd score 40 a season... it's more like 50." The following month he was named in Port Vale's best XI of the 2010s by local newspaper "The Sentinel". On 5 January, he tweeted a World War III prediction that "We invade Iran then Cuba then North Korea then the Rothchilds are crowned champions of every bank on the planet"; the FA concluded that these remarks amounted to Antisemitic canard and handed him a £3,500 fine and a six game ban to start at the beginning of the 2020–21 season. The club announced that they would appeal the ban, adding that "the Commission did not find that Mr. Pope had been intentionally discriminatory and noted that the FA had not alleged any such intent on his part".