[5] After returning from Germany Ipswich scheduled pre-season friendlies with a number of English sides.

New signings including Tomáš Holý and James Norwood saw a change to the first-team squad, following the departure of a number of first team players at the end of the previous season.

[6] The season began on the 3 August, with Ipswich traveling away to face Burton Albion at the Pirelli Stadium.

[7] The following week saw Ipswich host Sunderland in the club's first home game of the season at Portman Road.

[15] Summer signing Kane Vincent-Young picked up a groin injury during the win away at Fleetwood, which forced him to leave the field.

[16] Ipswich began their 2019–20 FA Cup campaign on 9 November after being drawn at home to divisional rivals Lincoln City, with the first-round match ending in a 1–1 draw, setting up a replay as a result.

[19] Ipswich suffered from a poor run of form over November and December, starting with a 2–2 draw at home to Blackpool followed by a 0–0 draw with then league leaders Wycombe Wanderers, with a goal by Ipswich captain Luke Chambers being controversially ruled out for offside.

[21] Despite progression in the EFL Trophy, the poor league run continued as Ipswich failed to win in eight consecutive league games from mid November to New Year's Day, including an FA Cup exit to Coventry City on 10 December following a replay after a 1–1 draw.

[27] The following run saw a huge decline in results for Ipswich, defeats to promotion rivals Peterborough United and Sunderland followed by a 0–0 draw away to AFC Wimbledon.

[4] Supplier: Adidas / Sponsor: Magical Vegas (chest), East Anglian Air Ambulance (back), Nicholas Estates (shorts) Age listed below are accurate as of 4 May 2020 The club's pre-season schedule was confirmed in June 2019.

The teams competing in the 2019 Interwetten Cup included Ipswich Town, Fortuna Düsseldorf, SV Meppen and FC Utrecht.

[35] The second round draw was made live on 11 November from Chichester City's stadium, Oaklands Park.