Former Ipswich Town loanees Keanan Bennetts and Troy Parrott were relegated with SV Wehen Wiesbaden and Excelsior respectively.
Both teams were handed heartbreaking defeats in the play-offs, with the former falling out of the 2. Bundesliga while the latter was relegated from the Eredivisie.
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Bennetts was recently released by Wehen Wiesbaden, having joined the German side from Darmstadt 98 last summer. He was unable to prevent them dropping to the third tier.
He featured in their relegation play-off games against Jahn Regensburg, who won 4–3 on aggregate to seal promotion to the second tier.
The 25-year-old winger spent the 2020/21 season at Portman Road on loan from Borussia Mönchengladbach, making 30 appearances for the Blues and scoring one goal.
Parrott, on the other hand, spent last season on loan at Excelsior from Tottenham Hotspur. He has had a whirlwind fortnight over in the Netherlands.
Having finished 16th in the Dutch top flight this season, Excelsior were involved in a seven-team play-off to decide the final spot in the division for the 2024/25 campaign.
They went on to beat ADO Den Haag 9-2 on aggregate in their first tie, with Parrott scoring a hat-trick in the second of those games.
That set up the clash with NAC in the deciding tie, only to lose 6-2 in the first leg away from home before the Dubliner almost helped them complete a remarkable comeback in the second leg – scoring another treble as they won 4-1. It wasn’t enough, however, as they lost 7–6 on aggregate.
The Republic of Ireland international finished the season with 17 goals in 32 outings. He now returns to Spurs with one year left on his contract.
He scored two goals in 18 games during his loan spell with the Blues in 2021 from the North London club.