Wood made his first start under new manager Markus Gisdol on October 25 in their second round DFB-Pokal match against Hallescher FC, scoring twice in the 4–0 victory. However, their problems in the league persisted, culminating in Wood being sent off in his first Bundesliga start under Gisdol, coming five days later at FC Köln. After the match, Gisdol told reporters that Wood's red card, given when he elbowed Köln defender Dominique Heintz in the stomach, was "inexcusable", and Wood was handed a three-match ban by the DFB. After the Cologne-match, Hamburg won three of their six remaining matches with Wood scoring one goal in the 2-1 win against FC Schalke 04 on matchday 16. Hamburg finished the year ranked 16th. In the following year, Hamburg started with two defeats against VfL Wolfsburg (0-1) and FC Ingolstadt both away (1-3), before the Northern Germans won six of the following ten matches and climbed to 13th. Wood scored a goal during this time against Borussia Mönchengladbach in a 2-1 victory. The following four matches ended with three defeats and one draw, placing Hamburg in 16th after matchday 32. In the penultimate matchday, Hamburg drew 1-1 against FC Schalke 04 away, after the goal of Pierre-Michel Lasogga in injury time. Before the goal of Lasogga, Bobby Wood had an opportunity to equalize. Through the draw, Hamburg saved themselves from relegation. The last matchday one week later, Hamburg won 2-1 against VfL Wolfsburg and saves with the 14th rank before the relegation. In the 2017-18 season, Hamburg lost in the first round of the DFB-Pokal (German Cup) against the third-tier side VfL Osnabrück 1-3. Hamburg won their first two matches with Bobby Wood scoring a goal in the 3-1 win away against Cologne. In the remaining matches of the first half of the season, Hamburg won only two matches and ranked 17th. In the second season-half, manager Markus Gisdol was sacked after a 0-2 defeat against Cologne at home. His successor Bernd Hollerbach was sacked after seven matches without a victory. The new president of the club, Bernd Hoffmann, sacked CEO Heribert Bruchhagen and the director of sport, Jens Todt, and the successor of Hollerbach became Christian Titz, former head coach of the reserve team.