diff --git a/src/config_directives.c b/src/config_directives.c
index 960dee5b..20b880ed 100644
--- a/src/config_directives.c
+++ b/src/config_directives.c
@@ -29,6 +29,7 @@ CFGFUN(criteria_init, int _state) {
     criteria_next_state = _state;
 
     DLOG("Initializing criteria, current_match = %p, state = %d\n", current_match, _state);
+    match_free(current_match);
     match_init(current_match);
 }
 
diff --git a/src/manage.c b/src/manage.c
index 5cfe490e..0dec2844 100644
--- a/src/manage.c
+++ b/src/manage.c
@@ -294,6 +294,7 @@ void manage_window(xcb_window_t window, xcb_get_window_attributes_cookie_t cooki
         if (match != NULL && match->insert_where != M_BELOW) {
             DLOG("Removing match %p from container %p\n", match, nc);
             TAILQ_REMOVE(&(nc->swallow_head), match, matches);
+            match_free(match);
         }
     }
 
diff --git a/src/match.c b/src/match.c
index 8da3c1ea..1cdd478f 100644
--- a/src/match.c
+++ b/src/match.c
@@ -238,21 +238,13 @@ bool match_matches_window(Match *match, i3Window *window) {
  *
  */
 void match_free(Match *match) {
-    /* First step: free the regex fields / patterns */
     regex_free(match->title);
     regex_free(match->application);
     regex_free(match->class);
     regex_free(match->instance);
     regex_free(match->mark);
     regex_free(match->window_role);
-
-    /* Second step: free the regex helper struct itself */
-    FREE(match->title);
-    FREE(match->application);
-    FREE(match->class);
-    FREE(match->instance);
-    FREE(match->mark);
-    FREE(match->window_role);
+    regex_free(match->workspace);
 }
 
 /*
@@ -264,16 +256,19 @@ void match_parse_property(Match *match, const char *ctype, const char *cvalue) {
     DLOG("ctype=*%s*, cvalue=*%s*\n", ctype, cvalue);
 
     if (strcmp(ctype, "class") == 0) {
+        regex_free(match->class);
         match->class = regex_new(cvalue);
         return;
     }
 
     if (strcmp(ctype, "instance") == 0) {
+        regex_free(match->instance);
         match->instance = regex_new(cvalue);
         return;
     }
 
     if (strcmp(ctype, "window_role") == 0) {
+        regex_free(match->window_role);
         match->window_role = regex_new(cvalue);
         return;
     }
@@ -339,11 +334,13 @@ void match_parse_property(Match *match, const char *ctype, const char *cvalue) {
     }
 
     if (strcmp(ctype, "con_mark") == 0) {
+        regex_free(match->mark);
         match->mark = regex_new(cvalue);
         return;
     }
 
     if (strcmp(ctype, "title") == 0) {
+        regex_free(match->title);
         match->title = regex_new(cvalue);
         return;
     }
@@ -362,6 +359,7 @@ void match_parse_property(Match *match, const char *ctype, const char *cvalue) {
     }
 
     if (strcmp(ctype, "workspace") == 0) {
+        regex_free(match->workspace);
         match->workspace = regex_new(cvalue);
         return;
     }
diff --git a/src/regex.c b/src/regex.c
index 913519be..24846981 100644
--- a/src/regex.c
+++ b/src/regex.c
@@ -64,6 +64,7 @@ void regex_free(struct regex *regex) {
     FREE(regex->pattern);
     FREE(regex->regex);
     FREE(regex->extra);
+    FREE(regex);
 }
 
 /*