Three police officers were injured and nine arrests were made as Tottenham and Ajax fans clashed outside the north London side's stadium before and after the Champions League semi-final clash.
Mauricio Pochettino's side fell to a 1-0 home defeat in the first leg of the tie thanks to a goal from Donny van de Beek, but the night was marred by unsavoury scenes before the match kicked off.
According to the Daily Mirror, three police officers were injured whilst attempting to arrest missile-throwing fans before the match started, and fans from both sides were caught on camera clashing after the game.
Scotland Yard later confirmed that nine arrests were made on Tuesday night, with a Metropolitan Police spokesman confirming that a group of supporters began throwing missiles outside the new Tottenham stadium at approximately 7.15 pm.
As officers intervened, four individuals were arrested, with a further five arrests made prior to the game's 8pm kick-off in relation to other incidents.
Three police officers have been injured while arresting missile-throwing football fans ahead of a Champions League match in north London. Scotland Yard said nine arrests were made before Tottenham's semi-final clash with Dutch side Ajax on Tuesday night.— LBC Breaking (@lbcbreaking) April 30, 2019
The unsavoury scenes continued after the game as well, with cones and glass bottles being thrown as fans clashed following Pochettino's side's defeat.
Van de Beek's first-half strike gave Ajax a crucial away goal, with Spurs now facing a daunting task in the return leg in Amsterdam if they are to reach their first ever Champions League final.
The visitors' dominant opening period saw them rewarded with a goal, with Spurs boss Pochettino later admitting in his post-match press conference that he had gotten his tactics wrong.
The north London side travel to the Netherlands for the second leg next Wednesday, but first face Eddie Howe's Bournemouth at Dean Court on Saturday afternoon, as they attempt to retain their spot in the Premier League top four.