Arsenal entered the 2019-20 season as defending WSL champions, having won the title for the first time in seven years the previosu season. This secured the club a place in the UEFA Women's Champions League for 2019-20.
The first pre-season friendly was on 28 July, against Bayern München in the Emirates Cup. This was played as a double-header with the men's team, who played later that afternoon. The team were still missing their Dutch and English internationals following the World Cup, and had only been in pre-season for one and a half weeks. Bayern won the match 0–1. During the match Danielle Carter was taken off the field on a stretcher late in the second half. It was later revealed that she had sustained a second ACL injury, she had just returned after almost a year out from a previous ACL injury.
Updated to match(es) played on 17 November 2019.
The 2019-20 WSL season started with a home game against West Ham United which Arsenal won 2-1 goals from Beth Mead and debut signing Jill Roord. The second match was an away game against newly promoted Manchester United, managed by former Arsenal player Casey Stoney. The tight match ended with a 89th minute goal from Daniëlle van de Donk sealing a second victory. Matchday three saw Brighton & Hove Albion visiting the Gunners at Meadow Park, Kim Little, Vivianne Miedema, Van de Donk and Jordan Nobbs scoring a goal each during the 4-0 victory.
The fourth match took place after the October international break and saw Arsenal visit Chelsea at Kingsmeadow. Van de Donk scored an early goal however Chelsea scored two goals during the second half ending the Gunners' run of 11 matches unbeaten. The team dropped down to third in the league as a result of the defeat. The next league match was at home against Manchester City who were the only side who hadn't dropped any points in the league. Miedema scored the winner in the 1-0 victory but Nobbs came very close in the latter stages of the second half, missing a few yards from the goal. Arsenal moved into second place in the league, one point behind Chelsea.
Matchday six took place on the Women's Football weekend and saw Arsenal travel to Tottenham Hotspur for the first North London Derby of the WSL. Second half goals from Little and Miedema secured a 2-0 victory but the team slipped to third in the league, still only one point from the top.