diff --git a/src/search_filter/date_filter.py b/src/search_filter/date_filter.py
index 06cf8878..aec28e01 100644
--- a/src/search_filter/date_filter.py
+++ b/src/search_filter/date_filter.py
@@ -28,7 +28,8 @@ def date_filter(query, entries, embeddings):
         return query, entries, embeddings
 
     # remove date range filter from query
-    query = re.sub(date_range_regex, '', query)
+    query = re.sub(f'\s+{date_regex}', ' ', query)
+    query = re.sub(r'\s{2,}', ' ', query).strip()  # remove multiple spaces
 
     # find entries containing any dates that fall with date range specified in query
     entries_to_include = set()
@@ -38,7 +39,7 @@ def date_filter(query, entries, embeddings):
             # Convert date string in entry to unix timestamp
             date_in_entry = datetime.strptime(date_in_entry_string, '%Y-%m-%d').timestamp()
             # Check if date in entry is within date range specified in query
-            if query_daterange[0] <= date_in_entry <= query_daterange[1]:
+            if query_daterange[0] <= date_in_entry < query_daterange[1]:
                 entries_to_include.add(id)
                 break
 
diff --git a/tests/test_date_filter.py b/tests/test_date_filter.py
index 272643cf..615eeb5b 100644
--- a/tests/test_date_filter.py
+++ b/tests/test_date_filter.py
@@ -3,10 +3,57 @@ import re
 from datetime import datetime
 from math import inf
 
+# External Packages
+import torch
+
 # Application Packages
 from src.search_filter import date_filter
 
 
+def test_date_filter():
+    embeddings = torch.randn(3, 10)
+    entries = [
+        ['', 'Entry with no date'],
+        ['', 'April Fools entry: 1984-04-01'],
+        ['', 'Entry with date:1984-04-02']]
+
+    q_with_no_date_filter = 'head tail'
+    ret_query, ret_entries, ret_emb = date_filter.date_filter(q_with_no_date_filter, entries.copy(), embeddings)
+    assert ret_query == 'head tail'
+    assert len(ret_emb) == 3
+    assert ret_entries == entries
+
+    q_with_dtrange_non_overlapping_at_boundary = 'head dt>"1984-04-01" dt<"1984-04-02" tail'
+    ret_query, ret_entries, ret_emb = date_filter.date_filter(q_with_dtrange_non_overlapping_at_boundary, entries.copy(), embeddings)
+    assert ret_query == 'head tail'
+    assert len(ret_emb) == 0
+    assert ret_entries == []
+
+    query_with_overlapping_dtrange = 'head dt>"1984-04-01" dt<"1984-04-03" tail'
+    ret_query, ret_entries, ret_emb = date_filter.date_filter(query_with_overlapping_dtrange, entries.copy(), embeddings)
+    assert ret_query == 'head tail'
+    assert ret_entries == [entries[2]]
+    assert len(ret_emb) == 1
+
+    query_with_overlapping_dtrange = 'head dt>="1984-04-01" dt<"1984-04-02" tail'
+    ret_query, ret_entries, ret_emb = date_filter.date_filter(query_with_overlapping_dtrange, entries.copy(), embeddings)
+    assert ret_query == 'head tail'
+    assert ret_entries == [entries[1]]
+    assert len(ret_emb) == 1
+
+    query_with_overlapping_dtrange = 'head dt>"1984-04-01" dt<="1984-04-02" tail'
+    ret_query, ret_entries, ret_emb = date_filter.date_filter(query_with_overlapping_dtrange, entries.copy(), embeddings)
+    assert ret_query == 'head tail'
+    assert ret_entries == [entries[2]]
+    assert len(ret_emb) == 1
+
+    query_with_overlapping_dtrange = 'head dt>="1984-04-01" dt<="1984-04-02" tail'
+    ret_query, ret_entries, ret_emb = date_filter.date_filter(query_with_overlapping_dtrange, entries.copy(), embeddings)
+    assert ret_query == 'head tail'
+    assert ret_entries == [entries[1], entries[2]]
+    assert len(ret_emb) == 2
+
+
 def test_extract_date_range():
     assert date_filter.extract_date_range('head dt>"2020-01-04" dt<"2020-01-07" tail') == [datetime(2020, 1, 5, 0, 0, 0).timestamp(), datetime(2020, 1, 7, 0, 0, 0).timestamp()]
     assert date_filter.extract_date_range('head dt<="2020-01-01"') == [0, datetime(2020, 1, 2, 0, 0, 0).timestamp()]