The east Londoners marched into a 3-0 lead at the break against previously unbeaten leaders, thanks to goals from Steve Summers (2) and Scott Warren.
Raiders rallied in the second half, with Jonny Blain (2) reducing the deficit to a single goal, but Chigwell held on to close the gap to just four points, still with a game in hand.
Danny Carr and Scott Ansher earned Brady Maccabi a 2-1 win over Scrabble for whom Dan Lewis replied.
In the Nathan Horwitz Division 2 Cup, Marshside progressed at the expense of local rivals Glenthorne, with Jason Rich (2), Fara Moghim, Justin Woolf and David Hyman giving them a 5-1 win.
Also into the hat for the next round are St John’s Wood Tigers, who dispatched Brady B 7-0 thanks to goals from Ashley Marks (2), Darryl Lazarus (2), Paul Herszaft, Grant Morgan and Adam Soller.
Maccabi London Lions B will join them, as a hat-trick from Michael Abraham and goals from Arthur Duke and Simon Black secured a 5-0 win over Temple Fortune.
-------------------
RESULTS
Maccabi Masters Football League, Division 1
Brady Maccabi A 2 Scrabble 1
North London Raiders 2 Chigwell Athletic 3
Nathan Horwitz MMFL Division 2 Cup, sponsored by Atlantis Travel
Brady Maccabi B 0 St John’s Wood Tigers 7
Glenthorne 1 Marshside 5
Temple Fortune 0 Maccabi London Lions B 5
--------------------
TABLES
DIVISION ONE
1. NL Raiders Pl. 10, W. 8, Pts. 25
2. Chigwell Athletic Pl. 9, W. 7, Pts. 21
3. ML Lions Pl. 8, W. 5, Pts. 16
4. Brady Maccabi Pl. 9, W. 4, Pts. 12
5. Scrabble Pl. 12, W. 2, Pts. 7
6. HMH Pl. 10, W. 1, Pts. 4
--------------------
DIVISION TWO
1. EHRS Stonegrove Pl. 11, W. 9, Pts. 28
2. ML Lions B Pl. 7, W. 6, Pts. 18
3. Marshside Pl. 11, W. 5, Pts. 17
4. Glenthorne Pl. 8, W. 5, Pts. 16
5. St John's Wood Tigers Pl. 11, W. 4, Pts. 14
6. Temple Fortune Pl. 10, W. 3, Pts. 9
7. Brady Maccabi B Pl. 10, W. 1, Pts. 5
8. Hendon Harriers Pl. 8, W. 1, Pts. 3