diff --git a/lib/gitlab/conflict/file.rb b/lib/gitlab/conflict/file.rb
index cdbb63f626ff2c40fc14d1995621f7aaa31355ac..6284b0dd3776966d52df087e614ef2b387549eb2 100644
--- a/lib/gitlab/conflict/file.rb
+++ b/lib/gitlab/conflict/file.rb
@@ -79,6 +79,9 @@ module Gitlab
       def sections
         return @sections if @sections
 
+        # Any line beginning with a letter, an underscore, or a dollar can be used in a
+        # match line header. Only context sections can contain match lines, as match lines
+        # have to exist in both versions of the file.
         candidate_match_headers = lines.map do |line|
           " #{line.text}" if line.text.match(/\A[A-Za-z$_]/) && line.type.nil?
         end
@@ -89,19 +92,24 @@ module Gitlab
         @sections = chunked_lines.flat_map.with_index do |(no_conflict, lines), i|
           section = nil
 
+          # We need to reduce context sections to CONTEXT_LINES. Conflict sections are
+          # always shown in full.
           if no_conflict
             conflict_before = i > 0
             conflict_after = chunked_lines.peek
 
             if conflict_before && conflict_after
+              # Create a gap in a long context section.
               if lines.length > CONTEXT_LINES * 2
                 head_lines = lines.first(CONTEXT_LINES)
                 tail_lines = lines.last(CONTEXT_LINES)
 
+                # Ensure any existing match line has text for all lines up to the last
+                # line of its context.
                 update_match_line_text(match_line, head_lines.last, candidate_match_headers)
 
+                # Insert a new match line after the created gap.
                 match_line = create_match_line(tail_lines.first)
-                update_match_line_text(match_line, tail_lines.last, candidate_match_headers)
 
                 section = [
                   { conflict: false, lines: head_lines },
@@ -111,7 +119,8 @@ module Gitlab
             elsif conflict_after
               tail_lines = lines.last(CONTEXT_LINES)
 
-              if lines.length > CONTEXT_LINES
+              # Create a gap and insert a match line at the start.
+              if lines.length > tail_lines.length
                 match_line = create_match_line(tail_lines.first)
 
                 tail_lines.unshift(match_line)
@@ -119,10 +128,14 @@ module Gitlab
 
               lines = tail_lines
             elsif conflict_before
+              # We're at the end of the file (no conflicts after), so just remove extra
+              # trailing lines.
               lines = lines.first(CONTEXT_LINES)
             end
           end
 
+          # We want to update the match line's text every time unless we've already
+          # created a gap and its corresponding match line.
           update_match_line_text(match_line, lines.last, candidate_match_headers) unless section
 
           section ||= { conflict: !no_conflict, lines: lines }
@@ -139,10 +152,13 @@ module Gitlab
         Gitlab::Diff::Line.new('', 'match', line.index, line.old_pos, line.new_pos)
       end
 
+      # Set the match line's text for the current line. A match line takes its start
+      # position and context header (where present) from itself, and its end position from
+      # the line passed in.
       def update_match_line_text(match_line, line, headers)
         return unless match_line
 
-        header = headers.first(line.index).compact.last
+        header = headers.first(match_line.index).compact.last
 
         match_line.text = "@@ -#{match_line.old_pos},#{line.old_pos} +#{match_line.new_pos},#{line.new_pos} @@#{header}"
       end
diff --git a/spec/lib/gitlab/conflict/file_spec.rb b/spec/lib/gitlab/conflict/file_spec.rb
index cf670b3182a5241e5d91a886e6e8fabead355a33..405b97686f5a162eaf1e67346bcfb7ba4fbc985d 100644
--- a/spec/lib/gitlab/conflict/file_spec.rb
+++ b/spec/lib/gitlab/conflict/file_spec.rb
@@ -86,19 +86,20 @@ describe Gitlab::Conflict::File, lib: true do
   end
 
   describe '#sections' do
-    it 'returns match lines when there is a gap between sections' do
-      section = conflict_file.sections[5]
-      match_line = section[:lines][0]
+    it 'only inserts match lines when there is a gap between sections' do
+      conflict_file.sections.each_with_index do |section, i|
+        previous_line_number = 0
+        current_line_number = section[:lines].map(&:old_line).compact.min
 
-      expect(section[:conflict]).to be_falsey
-      expect(match_line.type).to eq('match')
-      expect(match_line.text).to eq('@@ -46,53 +46,53 @@ module Gitlab')
-    end
+        if i > 0
+          previous_line_number = conflict_file.sections[i - 1][:lines].map(&:old_line).compact.last
+        end
 
-    it 'does not return match lines when there is no gap between sections' do
-      conflict_file.sections.each_with_index do |section, i|
-        unless i == 5
-          expect(section[:lines][0].type).not_to eq(5)
+        if current_line_number == previous_line_number + 1
+          expect(section[:lines].first.type).not_to eq('match')
+        else
+          expect(section[:lines].first.type).to eq('match')
+          expect(section[:lines].first.text).to match(/\A@@ -#{current_line_number},\d+ \+\d+,\d+ @@ module Gitlab\Z/)
         end
       end
     end